


Momentum

by Firebog



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Cas isn't clueless, Dean's giggle fits don't help the situation, First Time Sex, Hand Jobs, Human Castiel, Loss of Virginity, M/M, Making Out, Morning After, Sam to the rescue the next morning, Virgin Castiel, Worried Dean, also drinking doesn't help, but he tries to be serious, but the fine details escape him, sort of, terrible drunk awkward mood ruining first time sex
Language: English
Status: In-Progress
Published: 2014-08-24
Updated: 2014-09-18
Packaged: 2018-02-14 13:22:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 24,175
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2193348
Author URL: https://archiveofourown.org/users/Firebog/pseuds/Firebog
Summary: <blockquote class="userstuff">
              <p>It had started out innocently enough. Movie night: drinking and popcorn and PJs. <em>Innocent.</em> And then Dean had screwed that up by getting grabby and gropey and he was sure Cas was freaking out because Cas getting quiet was never a good thing. Dean was on the verge of apologizing and explaining how he was actually a huge asshole and none of this would ever happen again when Cas spoke up.</p><p>"Can we have sex?"</p>
            </blockquote>





	1. The Untouchables

**Author's Note:**

> This is AU in the sense that Sam closes the gates of Hell and nothing bad happens to him after. Cas goes directly to the bunker, nothing bad happens to him, and he doesn't get kicked out. And you know what while we're at it they rescued Linda Tran right away and she is recovering from her time as a captive by helping to hunt down the remaining demons on earth, and Charlie and Kevin basically become the bestest of nerd friends and bond over RPGs and Magic: The Gathering, and everyone decides to say screw it to Heaven's politics and they go back to hunting ghosts and monsters.
> 
> .....And I just realized I would really enjoy the adventures of Charlie and Kevin trying to educate Cas in pop culture before Dean sinks his hooks in and brain washes Cas with the 80s.
> 
> Yes there will be smut but it's less super emotional gentle introduction to sex and more mood ruined by being drunk, lack of experience, and awkward moments kind of sex.

**Summary for the Chapter:**

> It had started out innocently enough. Movie night: drinking and popcorn and PJs. See? _Innocent._ Dean could say with 100% certainty he hadn't planned this. If anything it was Sam's fault because Sam was a health freak and had to get up early to go _jogging,_ which apparently meant he couldn't stay up and watch the second movie and drink with them. It was definitely Sam's fault that there was an empty bottle of whiskey on the table and it was definitely Sam's fault that he was making out with Cas. Dean didn't know how they had gone from watching The Untouchables to making out but somehow it had happened. The Untouchables wasn't even a sexy movie.

It had started out innocently enough. Movie night: drinking and popcorn and PJs. See? _Innocent_. Dean could say with 100% certainty he hadn't planned this. If anything it was Sam's fault because Sam was a health freak and had to get up early to go _jogging_ , which apparently meant he couldn't stay up and watch the second movie and drink with them. This was totally Sam's fault.

And it was definitely Sam's fault that there was a mostly empty bottle of whiskey on the table. It was Sam's fault that he was making out with Cas because Dean couldn't explain how they had gone from watching The Untouchables to making out. It had just...happened...somehow. _The Untouchables wasn't even a sexy movie._ Alright, maybe he had a thing for Eliot Ness no matter who was playing him but that was entirely understandable. Who _wouldn't_ have a thing for Eliot Ness? Eliot Ness was a badass...kind of like Cas.

Dean scooched a bit closer to Cas and tried to angle his head a bit better so their teeth weren't gnashing. Cas wasn't exactly the best make out partner he had ever had but he was enthusiastic about it, which did make it fun. Dean hadn't made out like this since he was in high school; kind of sloppy and wet but fun and exciting and new.

Cas made a noise that sounded like it might be a question. Dean's eyes popped open to find Cas staring at him. Dean pulled back, wiping the back of his hand across his mouth. Cas spit. Gross– no, _hot_. He chuckled as he wiped his hand on his jeans, "Dude, you have to close your eyes when you make out. It's like rule number one of making out."

Cas squinted at Dean. That was a ridiculous rule. That sounded like something Dean had made up. He _liked_ watching Dean. He _liked_ making out with Dean. He didn't see why he couldn't do both. "Why? I _like_ watching you."

"Yeah, it was always _a little bit_ creepy waking up to find that out." Dean reached over to the coffee table to pour the last of the whiskey into their tumblers. The table seemed to shift and twist. He closed one eye as he poured. It definitely helped with his aim. He only spilt a little bit. He poured himself a generous triple shot while pouring a shot and a half for Cas. He set the now empty bottle down a little harder than he meant to but hey, it was empty, who cared if it broke? Definitely not him.

Cas eyed the two glasses. Dean had unfairly distributed the last of the whiskey. He liked whiskey...and...he _liked_ Dean. Even if Dean was trying to drink more than his fair share of whiskey...which he liked. Cas snatched up the glass with more. He enjoyed this. As an angel it had been a chore to drink until intoxication but now it was.... _pleasant_. He felt warm all over. He took a long sip enjoying that the whiskey didn't burn his throat anymore but warmed him up from the inside out– like watching Dean. "I watched you rake leaves once."

Dean stared completely and utterly at a loss for words. Cas had watched him rake leaves? Cas had watched him rake leaves! He burst out laughing. " _Wh-what?_ That's—"

Dean doubled over in laughter. He laughed for a good solid two minutes before he wiped his eyes and looked at Cas; a stray chuckle still escaping him. "You're joking right?"

"No. _I did_." Cas said adamantly. He refrained from mentioning that he had left eventually to make a deal with Crowley. He wanted to continue making out and he didn't think Dean would be amicable to that if he brought up his dealings with Crowley. Even if he had been forgiven for his acts. He squinted at Dean, carefully taking in his every feature and freckle. He took a sip of whiskey before adding, "I watched you rake leaves for approximately forty-seven minutes."

" _Of course_ you did." Dean said. He gave Cas's hair an affectionate ruffle then took the glass of whiskey off Cas. He sipped at it. _Of course_ Cas had watched him rake leaves for _approximately_ forty-seven minutes. Cas was his very own badass stalker angel. He started laughing again. Oh god, he'd had a stalker angel for years!

"What?" Cas asked, taking the glass back. He frowned. He _liked_ Dean. He didn't see why his concern for Dean's safety and his loyalty throughout the years was something to laugh at. He brought the glass to his lips– well he tried. He seemed to have misjudged his lips' location and distance and brought it to the side of his face instead. He pulled his head back and corrected the problem. He took a sip from the glass, thinking about all the times he had watched Dean. He wouldn't be able to do that anymore now that he was human. That pleasant warmth the whiskey brought on started to fade.

Cas started to make his confused and kind of upset face, which was not something Dean wanted to see tonight because they were having a sloppy make out session and frowning was not allowed. He tugged the glass of whiskey out of Cas's hand and set it down on the table then turned back to Cas. He grabbed Cas's face and pulled him into another deep kiss. He flicked his eyes open for a second to see Cas staring at him again. "Close your eyes, dude. Relax."

Cas narrowed his eyes at Dean. Dean was still holding his face in both hands. Cas tried to give Dean one of his best _I will not be trifled with_ looks but Dean just stared back and _didn't_ kiss him. Fine. If that was how Dean wanted to kiss he'd kiss that way.

Cas closed his eyes and was rewarded a few seconds later with Dean's lips against his own. Cas hummed his pleasure at the fortuitous turn of events. He leaned in closer to Dean but Dean kept leaning back. That _wasn't_ fair– just like Dean's dispensation of the whiskey. He was kissing the way Dean had told him to he shouldn't be punished for following instruction. It wasn't _fair_. His eyebrows drew together as Dean leaned further and further back. Cas followed Dean's lips, chasing the kiss, until he found himself grabbing at the side of the couch trying to stay upright. He was less than successful. His fingers didn't seem to be working the way they should be. He fell forward onto Dean.

Dean chuckled against Cas's lips when Cas fell on top of him. He bit at his own lips and smirked a little. Okay, so maybe making out with Cas was more than just _fun_ , it was actually kind of _awesome_. He opened his eyes to see Cas staring down at him looking... _vexed._ Yeah, that was it, _vexed_. He chuckled again. He was kissing Cas and Cas was _vexed_ about it. The chuckle turned into a snort of laughter. Goddamn he was drunk if he was laughing this much.

Cas started to squirm away and try to haul himself back upright. That wouldn't do. Dean's hands shot out to Cas's sides and held him still. This was where he wanted Cas, spread out across him and...and... _kissable_. He started to slowly rub his hands up and down Cas's sides. Jesus, Cas was _firm_.

Cas stared down at Dean. There was a question in Dean's eyes. Cas hesitated, not quite sure he had the right answer in mind. He had thought at first Dean was laughing at him for having fallen but...he let go of the side of the couch and sank down. Dean's hands slid around him. He let out a long sigh. He had definitely made the right choice. He let his muscles relax and his body spread out across Dean. Another long sigh escaped him. He could smell the whiskey on his own breath.

Cas tried to get his arms comfortable in this new position. He ended up with one braced beside Dean's head and the other sinking into the back of the couch– which they needed to clean as he discovered when his fingers touched something crumbly. Dean's hands slid under his shirt and rubbed at his back pulling him in tighter. It made Cas shiver and feel warmer than the whiskey. It was very nice. "Is this still making out?"

"Mmmm....more like half way to second base." Dean said. He slid his hands down to Cas's butt and pressed down before Cas could ask what that meant. He rolled his hips up. Cas let out a little shocked gasp. Dean grinned and leaned up to kiss him. This was freakin' sweet. They should do this more often.

Whatever half way to second base was Cas _liked_ doing it with Dean. Dean would flick his tongue into his mouth then pull it back encouraging Cas to chase after it with his own tongue. Half way to second base was made even better by the way Dean's hands slid up and down his backside, pressing down on his butt or groping along his sides— _Oh!_ and rocking his hips against Cas's as he was doing now. Forcefully. Repeatedly.

Cas pressed his own hips down; taking advantage of the friction and relishing the way it was causing jolts of pleasure to sing through him. Yes, he liked half way to second base. More than he liked whiskey but definitely not as much as he _liked_ Dean.

Dean strained his neck up trying to push as much of his tongue into Cas's mouth as humanly possible. He could feel the muscles in his neck start to cramp. He worked his way back trying to find the arm of the couch so he could rest his head on it. It'd be easier to make out that way with Cas– which was something he wanted to keep doing because making out with Cas was goddamned awesome and he was a total loser for not having done this earlier. He shoved a hand into Cas's hair and pulled him closer. He rolled his hips up in a slow grind. Cas groaned around Dean's tongue. The corners of Dean's lips curved up into an awkward smile. Why hadn't they done this before?

Cas felt like he might combust. It had been the whiskey earlier that had heated his stomach up but now there was a smouldering fire deep in his gut that he thought had little to do with the whiskey. He _liked_ it. If this was _half way_ to second base he would definitely be agreeable to whatever entailed second base...what were these bases for exactly?

Cas would have put more thought into what making out had to do with bases– were they military in origin? But Dean was dragging his hips back and forth across his own, sometimes pressing Cas down with two firm hands on his butt. It was all...it was all very _warm_. Everything Dean did was setting his very veins on fire.

Dean revelled in the little shivers and twitches he was getting out of Cas with a few good grinds of his hips. Seriously, why hadn't he done this before? Sure he may have thought about it. He may have been entertaining the idea since day one of Cas coming home but why the hell hadn't he _done_ anything about it until _now?_ They had missed out on _weeks_ of potential make out time. **Weeks**. That was way to long. He made a mental note to never let weeks go by again without making out with Cas.

With weeks to make up for Dean went for Cas with a renewed vigour. He shifted around trying to free his leg that was trapped between Cas and the back of the couch. Cas started to move like he was going to sit up. That was no good. Dean sunk one hand into Cas's hair and brought the other up to the back of Cas's neck. Cas relaxed back into the kiss. That was more like it.

Dean managed to get his leg free. He wrapped it around and managed to plant his foot between Cas's legs. He shifted a bit more and– there! Perfect leverage. An already deep kiss turned more frantic as Dean pumped his hips up. This was freaking awesome. He slid the hand on Cas's neck down to Cas's butt and pressed down. Holy fucking god. His hips snapped up a few times of their own accord chasing after the pleasure.

Cas felt like someone had kicked him in the chest. His heart sped up. Was this second base? Maybe second base was an allusion to the apex of the heart? He could feel blood pounding through his body just under the skin. He breathed hard through his nose. Dean kept up the ferocious speed. Cas pulled away with a gasp. He sat up and caught his breath. His skin felt like it was crawling with a million tiny lightening bugs.

Fuck. Fuck, he had ruined it hadn't he? Dean let out a pathetic whimper. Cas was staring at him thinking hard. Yeah, he had ruined it. They had just been making out then he had to go and make it weird. Dean mentally cursed himself for being an overeager sex freak. He was dry humping an ex-angel on the couch in the living room of the bunker! Cas was probably freaked right out. Oh jesus, Cas had been trying to _get away_ from him earlier and he had pulled him down and _made_ him stay. Dean stared up at Cas terrified by what Cas was going to say but Cas stayed quiet. Dean was about to start apologizing for all the weird grabby-gropey-kind-of-humpy making out when Cas spoke up.

"Can we have sex?"

**Notes for the Chapter:**

> Sorry to people who are following my series and were hoping this was an update for that.


	2. Start with the socks

**Summary for the Chapter:**

> Cas waited for Dean to say something. He could see the thoughts passing behind Dean's eyes but he didn't know what they were. If he had still been an angel he would have been tempted to read Dean's mind. He watched the glassy look in Dean's eyes turn hard. Despite the odd disconnected puffy feeling in his cheeks Cas felt his face drop. Dean was going to say no.

**Notes for the Chapter:**

> I'm posting these as I proof read them. The whole thing should be up in a day or two.

"Can we have sex?"

Dean froze for a moment - eyes wide in shock - before he burst out laughing. He tried to sit up but his giggle based convulsions had him sliding off the couch to the floor with a thump. He clutched at his stomach as he laughed so hard it hurt. His laughter turned to almost silent wheezing when Cas bent down to stare at him confused. He had been worried about making out? He could feel tears leaking down his face as he tried to control his laughter. Leave it to Cas to just blurt something like that out. _Can we have sex?_ Dean snorted just thinking about it.

Cas watched quietly, not sure what he had done. He had watched humans for a very long time. He knew quite often humans kissed without intending to have sex but Dean had...he lost track of his thoughts as he thought of the way Dean had ground their hips together. He shook his head. Dean had seemed agreeable to more than kissing but now he was laughing. Clearly he had misinterpreted the situation.

With a final painful huff Dean got himself under control. _Can we have sex?_ A last chuckle erupted from him. And he had thought Cas was freaked out. On the topic of Cas, why was he being so quiet? Dean glanced up to Cas's face. Cas looked downtrodden. Dean felt like an asshole for laughing. He grabbed onto the coffee table as he tried to stand. The room spun. He got as far as sitting on his knees in front of Cas. Alright. He didn't really want to stand anyway.

Dean stared up into Cas's eyes and realized that _Can we have sex?_ was exactly why he hadn't made out with Cas before tonight because they _could_ have sex. The world wasn't ending and nothing was out to get them beyond the usual monsters. He didn't have any plans in the near future to sell his soul or something equally as dumb and Cas was at the bunker to stay. They _could_ have sex— and Dean could screw it up.

Cas waited for Dean to say something. He could see the thoughts passing behind Dean's eyes but he didn't know what they were. If he were still an angel he would have been tempted to read Dean's mind. He watched the glassy look in Dean's eyes turn hard. Despite the odd disconnected puffy feeling in his cheeks Cas felt his face drop. Dean was going to say no.

Alright. So...they _could_ have sex. Dean was sure about that part at least. It was the _should_ they have sex part he wasn't sure about. He swivelled around and grabbed a glass of whiskey off the table. He drained the glass. He set it down, grabbed the other glass, and finished that one off too. He turned back to Cas. _Oh._ His eyes went wide.

Dean breathed in sharply. Cas's hair was a mess - and that was saying something - his face was flushed, he was watching Dean with that weird intensity he had, his clothes were rumpled, he was griping the edge of the couch like his life depended on it, and...Dean's eyes lingered on Cas's lap. **Oh.** _Can we have sex?_ suddenly made a lot more sense. There was an impressive tent in the loose cotton of Cas's plain grey pajama pants– which had been Dean's not long ago. Dean's eyes flicked down to his own lap. The situation was about the same there. He looked back at Cas. _Can we have sex?_

Cas was sure Dean was going to say no right until Dean bent down and started tugging at his socks. Cas lifted his foot. Dean pulled his sock off and threw it across the room. Did taking his socks off mean yes? That hard resolved look was still on Dean's face. Dean tapped his other leg. Cas lifted it up. Dean pulled the other sock off and tossed it over his shoulder. Then Dean stopped and sat back and stared...did that mean no now? Had Dean changed his mind?

Dean's hand slid up his leg and settled on his knee. That warm feeling started to spread through Cas again. Cas watched Dean's fingers flex and tighten, squeezing Cas's knee. His heart picked up a beat. Then suddenly Dean threw his weight onto that knee and pushed himself up. Dean grabbed at his shirt, fell into him as he climbed up off the floor, and pressed against his chest as he tried to find somewhere to hold on. Cas kept his hands down, clutching at the couch, not sure what he was supposed to do as Dean awkwardly straddled his legs.

Dean's weight settled onto his lap. Was this second base? ...maybe second base was supposed to be referring to the way his skin felt electrified. First base had felt like a mild static cling and second base - if that's what this was - felt like a shock off an appliance, but then why wouldn't they be called acids? Acids conducted electricity too. Dean set his hands on his neck and gently brought them up to cup his jaw then stared at him. Cas waited to see what Dean would do next but nothing happened. He let go of the couch and tentatively brought his hands up. He settled his hands on the top of Dean's hips. A smile flickered across that hard resolved look.

There was a certain amount of absurdity to the whole thing. There he was straddling an ex-angel, sitting in his lap, holding his face, and staring at him. Dean knew the next step was kiss him again but he had gotten caught up in those eyes. Cas finally blinked breaking Dean's trance. He tilted Cas's head up and kissed him. He ground his hips against Cas.

It was kind of weird having a dick pressing against him that wasn't his own but weird in a good way. If weird could be good...was weird good? Whatever. Dean didn't mind it. It was actually kind of hot knowing that he was 100% responsible for what was going on in Cas's pants. He rolled his hips forward trapping their dicks between them, rubbing against each other. Cas gave a little yelp of surprise. Dean chuckled and pulled back. He looked at Cas seriously, "Yeah, I think I can swing that."

Cas breathed hard when Dean let him go. Swing that? What was there to swing? Wait. Was that the answer to his question? Cas licked his lips and offhandedly wished there was more whiskey. "Does that mean yes?"

Dean smiled at him and leaned back but didn't answer him. Cas frowned. He just wanted an answer to his question. He wasn't sure what he was supposed to do otherwise. One of Dean's hands dragged down his chest. It paused on his stomach then suddenly Dean's hand was hard and warm against his penis. Cas's eyes squeezed shut. A soft groan escaped his throat as Dean started to stroke him through his pants.

Cas felt another shock of pleasure rip through him when Dean's fingers wrapped around his penis through the thin cotton of his pants. He just...if he...he rocked his hips up into Dean's hand. He let out a harsh, _Ah!_ This had to be second base. Maybe second base was an improper term for base pairs? This did feel like it was shaking him right down to his newly human DNA. Cas's eyes flew open when Dean suddenly stopped. Dean was grinning down at him.

"Yeah Cas, it means yes." Dean said then promptly heaved himself off Cas and stood up. He snatched up one of the glasses from the table and made his way over to the cabinet where they kept the booze. His short walk over was more of a wide arc with some serious listing to the right but he made it. He fumbled with the cap on the bottle of whiskey. The _nice_ whiskey. He didn't usually break into the nice whiskey when he was this drunk but tonight was special. Well, he was calling it special.

"Dean?"

"Huh?" Dean carefully poured himself a splash. He brought the glass to his lips and let it drain down his throat. He definitely needed some liquid courage tonight. Cas wanted to have sex. Cas was a dude. He had never slept with a guy before. He was terrified of screwing it up. What if he was so bad at it that Cas didn't want to have sex with him again?

"What does second base mean?"

Dean snorted with laughter but thankfully didn't completely lose it again. "Normally it means a handful of tits."

Cas jerked his head back trying to understand how on earth second base meant breasts. "...what?"

Dean laughed as he poured himself a larger drink then on second thought added more in case Cas stole his glass again.

Cas shook his head. How could second base refer to breasts? Was Dean making it up? He watched Dean fumble with the cap to the whiskey. "Is it a reference?"

"Sort of." Dean said clutching the glass to his chest. He grabbed onto every piece of furniture between the cabinet and Cas trying to make desperately clutching at things to stay upright look smooth. It didn't but he tried. He should get points for effort.

Cas felt his face warm up as Dean ambled closer. Dean came to a stop in front of him. His knees pressed against his own. Cas looked up at him. He breathed in sharply. _Dean_ was **_staring_** _back_. Cas tried to ask what the reference was. It came out barely above a whisper, " A reference from what?"

"Baseball." Dean said, spreading his legs and shuffling forward so that Cas's legs were trapped between his own.

"Baseball?" Cas repeated incredulously. That made even less sense. How were breasts and baseball related?

Dean lowered himself down back into Cas's lap. He took a sip of whiskey then stared into Cas's eyes. "Yeah."

Cas narrowed his eyes at that. Dean was definitely making it up. "That's ridiculous."

Dean barked out a laugh at how indignant Cas looked over baseball sex metaphors. He was shocked out of his laugh when he felt Cas's hand glide along his arm. Was Cas putting the moves on him? God, that was hot. Oh. Cas was trying to steal the whiskey. Well, he wasn't giving that up so easily. He brought the glass up to Cas's lips and tipped it up. Cas stared at him from over the rim of the glass. It sent a little thrill of pleasure through Dean's core.

Cas let the whiskey slosh over his tongue while he stared up at Dean. Dean stared back at him with wide glassy eyes. Cas felt his face heating up. _Dean_ was **staring** at him. Dean took the glass away from his lips and brought it up to his own once more. Cas watched as Dean tipped his head back and drank. He watched the way Dean's neck extended and flexed as he swallowed. Cas took in a sharp breath as his heart sped up. Oh yes, he liked whiskey and he liked whatever it was they had been doing - second base was a ridiculous term - but most of all he **_liked_** to watch Dean.

Dean nearly choked when he saw the look Cas was giving him. He didn't think Cas knew how to make that look. It was a textbook _I am undressing you in my mind_ leer. Dean agreed with the sentiment behind that look. He finished the whiskey. He dropped the empty glass to the couch then slid his hands under Cas's t-shirt and started working it up. He pulled it up. Cas's head popped out. His hair stood on end. How would anyone know they had had sex if Cas always looked like he had sex hair?

Dean ran his hands over Cas's chest and gave him another kiss. Cas was getting better at it. It wasn't _that_ sloppy and wet anymore. He pulled away and breathed for a moment, taking in Cas, before standing up. He looked down at Cas. Cas was staring up at him looking wide-eyed and amazed. "You sure you want to?"

Cas nodded. He had never actively sought out a sexual encounter but now that the experience had presented itself - and with _Dean_ \- he wasn't going to pass it up. Dean offered his hand. Cas took it. Dean pulled him up off the couch. The motion made Cas dizzy for a moment but he didn't care. They stood flush against each other and for once Dean didn't complain about personal space.

Dean grinned at Cas. So they were gonna do this. Okay. Cas pressed a hand to his side gently and slid it down. For a moment Dean thought Cas was going to try out being grabby, it made his chest tighten in anticipation. What was Cas going to grab? But then Cas's hand slid further down until he was half crouched over and had hooked the back of Dean's knee with his hand. Cas started pulling his leg up. Dean's hands shot out as he lost his balance. He grabbed onto Cas's shoulder's trying to stabilize himself.

"Cas..." Dean broke up in laughter again when Cas looked up at him. "What're you doing?"

"You took my socks off first." Cas explained yanking at Dean's sock. It caught on Dean's heel. Cas quickly discovered if he pulled slowly the sock came off with ease. He dropped it to the ground.

"Right. Always take your socks off first." Dean said seriously. He wondered how long he could get Cas to believe that.

Cas nodded and focused at the task at hand. It was harder than it looked. His fingers didn't want to cooperate and he found his eyes kept going out of focus.

Socks finally off - because that was important - Dean started ushering Cas towards his bedroom. It was the longest walk of Dean's life. They should have stopped drinking an hour ago. Neither of them could walk straight and clinging to each other wasn't making up for it. The worst part was having to back track to the bathroom at Cas's insistence. They had been so close to his bedroom and then they had needed to walk _all the way back down the hall._

But Cas had made up for it. Halfway back to his room Cas had slammed into him and shoved him against the wall and he totally got why Meg had looked stunned after. What the hell had that sloppy, wet, and innocent act been about earlier? Dean tucked his hands into the waist of Cas's pants and pushed them down. He felt Cas wiggle out of them as they kissed. When Cas finally had to come up for air Dean let out an appreciative moan, "Cas, you were holding out on me back on the couch."

Cas's response was to kiss him again then start tugging him along the hall. Dean was thankful Charlie was out of town at some concert and that Kevin and Linda had— oh thank god Linda wasn't in the bunker. Dean didn't have many hang ups about being naked in front of people when he knew he was going to get lucky but the thought of _Linda_ seeing him mortified him. She was practically the bunker's den mother these days. He thanked whoever might be listening that she was out with Kevin for the week then started to kick his pants off as he followed Cas.

\---

Sam's eyes flicked open when he heard the walls rattle. He sat up and listened. There was a second thump and hushed voices then a bang and Dean laughing. Sam rolled his eyes. He didn't know what the hell Dean was putting Cas up to this time but it was probably nothing good. He swung his feet out of bed and went to tell Dean off. After the first few days of getting Cas settled in Dean had made it his favourite pastime to try and get Cas to do the stupidest things by convincing him that all humans did it. Cas didn't fall for it. Usually.

"Dean! What the **_hell_** are you **_doing!?_** _"_ Sam stomped down the hall and rounded the corner. "It's four in the morning and— oh god."

Cas glared up from the floor naked. "Go away, Sam."

"Yeah, Sammy, go away." Dean grinned up from beside Cas- also naked. "Unless you want a show."

Sam made a disgusted face, " ** _No._** _"_

Dean convulsed into a case of the giggles.

Sam jerked his head back when Cas shot him a _I am trying to get laid here_ look. He didn't think Cas even knew what that look was let alone how to make it. His whole body shook in disgust. His friend and his brother getting it on? No thanks. He fled back to his room, Dean cackling and shouting after him.

Sam swung his bedroom door closed and leaned against it. He was never going to get that image out of his head; Cas and Dean naked on the floor, Cas giving him a death glare while Dean laughed his ass off. He shook his head. What the hell was wrong with his brother? Why did he have to be such an exhibitionist freak? Dean was going to corrupt Cas—

 _ **Fuck.**_ He really hoped Dean remembered this tomorrow morning. He did _not_ want to have to deal with the fall out if Dean woke up beside Cas and didn't remember how he got there. Maybe he should go back and try to separate them? He'd probably have to throw a bucket of ice water on them at this point.

Sam debated on going back but as time passed - and rather unnerving noises came from down the hall - he realized he had waited too long if he was really going to do something about it. His shoulders slumped. He crawled back into bed. He laid there for awhile staring at the ceiling. Dear god, he hoped Dean didn't fuck this up.


	3. Condoms and lube are a must

**Summary for the Chapter:**

> Okay. This was not going how Dean expected it to. Dean sat up and studied Cas. Cas looked like a hot mess on his bed, sprawled out, sex hair, kind of sweaty, and a wicked looking hard but he also looked confused and innocent and well....kind of the ultimate paradox of debauched virgin, "....Cas, what did you mean when you asked to have sex?"

**Notes for the Chapter:**

> (random shameless self promotion I also do tumblr [Brains for baby jesus](http://brainsforbabyjesus.tumblr.com/) which has nothing to do with jesus and everything to do with being a nine-legged semiautomatic groove machine! and sometimes I post updates/notes/research (love me some research) about various fics I'm working on)

Dean stumbled around in the dark looking for his bedside lamp. He stubbed his toe off the nightstand. Found it. He clicked the lamp on. He looked over his shoulder. Cas was standing in his doorway. Cas was standing in his doorway naked. With a hard on. And he was just sort of staring at Cas who was standing naked in his doorway with a hard on. Okay. They couldn't stand here forever. Dean sat down on his bed and motioned for Cas to come over.

Cas wobbled over and sat down beside him. Cas looked over at him shyly. Dean's stomach dropped. Jesus christ, Cas was a virgin. A fucking _drunk_ virgin. Suddenly things went from hilarious making out to dead fucking serious. All of Dean's worries about screwing things up tripled. What if he ruined sex for Cas **_forever?_**

A frightened look passed behind Dean's eyes. Cas tilted his head wondering why? Was Dean having seco— Cas was distracted from his thoughts when Dean leaned in and kissed him. Dean took his shoulders in hand and pressed them back, encouraging him to lay down. A pang of excitement went through Cas. The way Dean had ground his hips into him on the couch had been nice with layers of clothes between them. He suspected without any would be even better.

Except Dean didn't do that. Instead Dean twisted and moved around until they were both fully on the bed laying out on their sides with about a foot of space between them. Cas glared at the empty space between them. Maybe they should have stayed on the couch where there was too little space.

Dean reached a hand out to stroke along Cas's arm. "You still want to have sex?"

"Yes."

"You sure?"

"Yes."

"Really sure?"

"Yes, Dean. I'm really sure."

Dean studied Cas's face looking for signs that Cas might be lying. Cas didn't look like he was lying. If anything he looked annoyed. Dean kept stroking Cas's arm. "Because you don't have to if you don't want to."

Cas rolled his eyes and let out an agitated huff that smelled strongly of whiskey, " _I'm **sure**."_

Dean held his hand out defensively, "Okay, okay, I'll quit asking."

Dean leaned in and wrapped his arms around Cas pulling him in closer. He figured another make out session was in order to get that _I am done with your bullshit_ expression off Cas's face. When he pulled back a few moments later Cas's face was flushed pink with a dopey grin on his lips. He brushed the hair away from Cas's forehead. He chuckled softly to himself, "You know, I made a promise to you...five years ago? That I wouldn't let you die a virgin."

"Four years." Cas said automatically.

"Right." Dean said. It didn't faze him in the least that Cas would know that. He ran his hand along Cas's face. He grinned again, "Well don't ever say I don't keep my promises."

Cas chuckled. He reached out and pulled Dean back to him. He didn't want to talk he wanted to make out– and eventually have sex. Dean had _said_ they could and he wanted to. _With Dean_. He rolled his hips experimentally against Dean to see if it felt different with skin to skin contact. It did. He hissed as those thousands of nerve endings in his penis lit up starting a happy little inferno under his skin. He groaned when Dean started rubbing back against him. _This was so much better._

From the noises Cas was making Dean half expected feeling a big wet spot between them any second now but Cas just kept on making noise and grinding his hips as hard as ever. Jesus, if he was making noises like that he'd be embarrassed but coming from Cas they were freakin' _hot_.

Dean thought over how this whole thing should go down while they kissed. He wasn't sure how drunk Cas was, actually yes he was sure, they were _both_ roaring drunk. Which meant Cas might not know if something was going wrong. Dean on the other hand had experience in that department...sort of. He had been with a couple of girls who were into pegging. It couldn't be that different from a real dick, could it? He made a split second decision. He grabbed Cas's hands away from his face and pulled back. "Cas, you okay with fucking me?"

"I asked to didn't I?" Cas scoffed and tried to go back to kissing.

Dean grabbed him again because he was pretty sure Cas didn't get what he was saying. "Cas, I mean...ah....I want you to top."

Cas paused. The look on Dean's face told him this was a serious question. "Top?"

"You know..." Dean tried to search for another word. "...shove it in."

Cas stared for a moment. Was this more baseball terms, like second base? He tried to think of how shoving something and 'top' would relate to baseball. He couldn't think of anything. "Shove what?"

Okay, this was not going how Dean expected it to. Dean sat up and studied Cas. Cas looked like a hot mess on his bed, sprawled out, sex hair, kind of sweaty, and a wicked looking hard on but he also looked confused, wide-eyed, and innocent and well...kind of the ultimate paradox of debauched virgin. "....Cas, what did you mean when you asked to have sex?"

"That I wanted to experience sex." Cas said sitting up. He set his hand on Dean's leg. "Preferably with someone I trust."

Dean stared, more than a little shocked. "...you trust me?"

Cas chuckled and gave Dean an affectionate grin. "Of course I trust you."

Dean felt his face heat up. Cas trusted him. He rubbed a hand over his face to try and make the blush go away. It was stupid. Of course Cas trusted him. The dude had put his life in his hands more than a few times. It just...it felt different when it was sex and not life or death. "Okay.....okay but what _sort_ of sex did you have in mind when you asked?"

"I don't know...." Cas said thoughtfully. He hadn't really thought it out that far. He had some vague ideas but no specifics. He just wanted to experience sex. With Dean. He didn't particularly care what kind, just as long as Dean wanted to do it too. "Manual? Intercrural perhaps?"

Inter-what? Dean worried about what sort of kinky websites Charlie was showing Cas. "Inter-crucible?"

"Intercrural." Cas ran his hands along the inside of his thighs. "It's when the thighs are used to stimulate the penis."

"Oh..." Dean watched Cas slide his hands along his legs. He felt his dick give an interested twitch. Cas obviously had no idea what he looked like doing that. Dean gulped and tried to put the image out of his head. He was having a serious discussion about _sex_ with a _virgin_. He needed his head out of the gutter. ...what had they been talking about? Inter...crucial? Something like that. Dean hadn't realized that thigh sex even had its own name and if that was what Cas wanted...that was actually pretty tame. Wow, he had _really_ misunderstood what Cas wanted out of this. Thank fucking god he had asked. "Oh. I thought...."

Cas tilted his head, curious about what Dean had thought. He waited for Dean to finish his sentence.

"I mean...I thought....well....you know...?" Dean said shrugging awkwardly.

"...no?" Cas shook his head. He couldn't mind read anymore and Dean hadn't liked it even when he could.

"I thought you meant..." Dean trailed off as his face turned red. His neck started to heat up. This shouldn't be that hard to say. He talked about sex all the time in front of Cas. Jesus fucking christ, why was this so embarrassing tonight? Probably because Cas was staring at him wide-eyed and innocent and wasn't blinking. Did Cas _ever_ blink? "I thought you meant.....anal."

Cas sat very still as his eyes darted across Dean's face. He ran the conversation over in his head. Top. Shove it in. Anal. Now he got it. "Oh! I see. _Anal intercourse_. And you want me to be the penetrating partner?"

"Yeah." Dean rubbed at his neck.

"Of course Dean, however you'd like." Cas said. He wanted to touch Dean's face but with how red it was Cas didn't think he'd like that. He chose a more angelic option, sit quietly and wait.

Dean looked around the room, anywhere but at Cas, until he felt the heat in his face drain away. He took a breath before he looked at Cas. Cas was watching him...but that's what Cas liked to do, right? For forty-seven minutes at a time. He felt another fit of laughter coming on but managed to stop it before he got carried away. He set a hand on Cas's arm. "Cas, do _you_ want to?"

"Yes." It hadn't occurred to Cas until Dean had brought it up but he would happily have anal intercourse with Dean if Dean wanted to. It really didn't matter to him what kind of sex they had as long as it was enjoyable for both of them. "As long as you want to too."

Dean grabbed Cas's face between his hands and started kissing him again. He broke away after a moment and leaned his forehead against Cas's, "Yeah....I want to."

With that Dean got up to dig out a condom and lube from his dresser drawer. He rummaged around for a moment then came back to the bed. He was holding an unopened box of condoms in one hand and a bottle of lube in the other. Right. So it was just him and Cas. With condoms and lube. In his room. Alone. Okay. He was really gonna do this. Thank you, liquid courage. Dean scratched at the plastic packaging of the box of condoms until he tore a hole in it. He ripped it off and opened up the box. He pulled out a ribbon of condoms and tore one off.

"Can I?" Cas asked as he watched Dean open the box. He wanted to experience sex - _with Dean_ \- and putting a condom on was an integral part to quite a bit of human sex.

Dean tossed the condom over to Cas, "Sure."

Cas opened it carefully. It smelled funny and had an almost greasy feel to it. He squinted down at it for a moment studying it in the palm of his hand before he picked it up and started trying to roll it over his penis.

Dean grabbed Cas's hand, "No. It's backwards."

"What?" Cas looked down at the condom. It looked much the same one way or another.

"It's backwards." Dean said again, easing Cas's hand away from his cock. "You have it the wrong way."

Cas held it up in front of his face and flipped it over one way then the other. He set it in his palm again and looked down at it. "How can you tell?"

"It's...it just goes the other way." Dean tried to explain that they were rolled up a certain way but he couldn't find the words for it. He ended up just making a rolling motion with his fingers that confused Cas even more. He reached out for it, "Here. Let me do it."

Cas pulled his hand away when Dean tried to grab the condom. He wanted to have sex. This was a part of sex. He could do it. "No, I can do it. Tell me."

"Blow on it." Dean said.

Cas raised his hand up - the condom flat on his palm – and blew on its side. He didn't know how that was supposed to help.

Dean laughed, "No, the other way–" He reached for it again but Cas jerked back. "I mean hold it like–" He mimed holding something circular between his fingers.

Cas held it up on its side and blew a second time. It still didn't do anything. Dean tried to take it from him again. He shuffled away on his knees. He got caught up in Dean's bed sheets and fell over. Dean crawled over his legs still trying to take the condom. He shot Dean an annoyed look. He could do this on his own.

"Oh my god Cas, what are–" Dean straddled Cas legs and sat on them so he couldn't get away. Cas scowled but he managed to swipe the condom off him. "Watch."

Cas watched as Dean held the condom between his fingers and blew a little puff of air on one of the flat sides of the condom. The condom popped up. Cas still didn't know how Dean could tell it was backwards.

Dean flipped it over and blew on it again putting it wrong side out. He passed it down to Cas, "You try."

Cas tried from where he was half fallen over on the bed. He was quite pleased with himself when it popped up the same way it had for Dean. Dean nodded his approval and let him sit up. Cas pushed himself up and sat back on his knees. He moved to put it on but Dean grabbed his hands. His head fell back and he groaned in frustration. "What now? Why is this so difficult?"

"It's not difficult. You're drunk. I should have showed you how to do this earlier." It hit Dean again that Cas was _a drunk virgin_. A drunk virgin who didn't even know how to put a condom on. Fuck. And he was kind of a slut in comparison to Cas - okay in comparison to a lot of people - and this was an all around terrible idea. He was going to fuck this up and then Cas would go on with his human life thinking sex was horrible. "....maybe we should hold off on this."

" _No."_ Cas said firmly.

"Cas...I dunno. I mean. I'm up for it if you are." Dean scratched at the back of his neck. "But only if you want to. We don't _have_ to do this tonight."

Cas fixed Dean with a determined stare. He had come this far. He was going to figure this out. "Just tell me what I'm doing wrong."

Dean hesitated for a moment but Cas looked serious. He pointed to the little bubble on the end of the condom. "Grab the little...uh...nubby bit on top."

Cas glared at it. This was as ridiculous as baseball. He shoved the condom at Dean, "You do it."

Dean grinned. Cas looked supremely pissed off about a couple of inches of latex. As worried as he was about Cas it was actually kind of funny to watch. He put his hands up, "Nope, you said you wanted to."

Cas turned that glare at Dean.

Dean laughed. Cas turned his nose up and set about putting a condom on with the most determination Dean had ever seen....and somehow he managed to fuck it up. Dean watched as Cas managed to get it on but with part of it rolled under itself. Dean stared in disbelief, "Dude, I don't even know how you did that."

Cas glared at the thin piece of latex

Dean grabbed a new condom and tossed it to Cas, "Take it off, try again."

Cas sighed, "....do we have to use one?"

" ** _Yes_** _, we have to use one."_ Dean said immediately. Jesus christ, he wasn't going to pop Cas's cherry _and_ teach him bad habits.

"Why?" Cas asked peeling the first condom off. He set it aside, "I was an angel until very recently, you know. I wasn't capable of carrying diseases."

"Yeah, and now you're human." Dean was starting to think it was probably a good thing Cas had asked him to have sex. He didn't want to think about what might have happened if they had gone out to a bar tonight.

"And I haven't had sex since I've become human." Cas carefully tore open the new foil packet. He glared at the condom. "...or before."

"Yeah well, I have. You know where I've been?" Dean said, brushing a hand down himself. Honestly the answer to that question was not something even he liked to dwell upon some days.

"...mostly." Cas said evasively.

Dean gave him a cross-eyed look, "Okay, I'm not gonna ask about that, cuz that's a little creepy, but the point is _mostly_ isn't one hundred percent. So we're using a condom."

Cas grumbled. He hadn't realized there were so many rules for sex. Humans made it look easy.

Dean watched Cas fiddle with the second condom. What the hell was Cas doing? A few moments went by and it was obvious that Cas didn't know what he was doing either. Cas's shoulders drooped and he stared at Dean pleadingly. Dean sighed and took pity. He grabbed a new condom because Cas had pretty much destroyed the other one. He opened it up and took Cas's dick in hand. He started working the condom down. It was a little strange putting a condom on someone else. Cas made funny little breathy noises as he rolled it down. Dean grinned, "Like that?"

Cas breathed hard through his nose, " _Yes."_

Dean smiled and licked his lips. Okay. He hadn't screwed this up so far. Cas sounded like he was enjoying himself. Dean sat back. Alright, so Cas was ready now he just had to...oh yeah... He looked over at the lube. Half the fun of getting pegged had been having a girl stretch him open and lube him up while sucking his dick but he wasn't sure how he felt about Cas giving him a blow job the same night he lost his virginity and he really didn't want to trust a drunk virgin to work him open when it was his own butt on the line.

Cas watched as Dean's face went from looking pleased to serious. Had he done something wrong? "....Dean?"

Dean glanced up. Cas looked worried. He realized he had been frowning at the lube. He flashed a smile at Cas then scooped the lube up. He flicked the cap open and squirted some out onto his fingers. He'd never done this to himself before but he had done it to enough chicks that he wasn't too worried about doing it right. He knew how to do it. He shifted around and settled on kneeling with his legs spread a bit. That seemed like it'd be the easiest way to do it. He took another breath and just went for it. He wasn't surprised that it felt good, he knew it would, but he was surprised at how easy it was to get the first finger in. He made a little noise at the back of his throat then remembered he had an audience. He looked over to find Cas was watching him. Dean winked, "Enjoying the show?"

"...I....don't....know...." Cas watched fascinated. He was definitely aroused but he wasn't sure if it was because of what Dean was doing or because he was _watching Dean_. Either way it was... _fascinating_. Dean's chest would heave each time he pushed his fingers in and sometimes he let out a soft sigh and...it was _very fascinating_ to watch.

Dean chuckled. Cas looked torn between taking notes and wanting to jump him. He waved Cas closer then grabbed Cas's dick with his other hand, measuring how much he'd have to stretch himself open. He pointed at the lube and motioned at Cas to pick it up, "Grab that would ya? And squirt some on."

Cas grabbed the bottle and promptly squeezed about a quarter of it onto Dean's open hand.

"Whoa! Jesus! Not that much!" Dean yanked his fingers out of himself to grab the bottle of lube away from Cas. Cas was Captain Obvious most days but he was Lieutenant Literal by night. Dean probably should have been a little more clear about how much _some_ was.

"Sorry." Cas's shoulders sank. He just wanted to try having sex and so far he couldn't put a condom on and he had wasted Dean's personal lubricant. He was terrible at this.

"It's okay, man." Dean dragged his fingers through the lube and worked some into himself. He looked down at the rest in his hand and shrugged. Might as well put it to use. Besides, he'd have to lube Cas up too anyway. He clapped a hand to Cas's dick and gave it a few pumps before it struck him that Cas had hands too. He let go of Cas and slopped some lube onto himself. He grabbed Cas's hand, grinning at the lube he got all over him, and placed Cas's hand on his dick. Cas didn't move. Dean leaned down to check Cas's face. Cas was making squinty eyes at his dick. "That okay?"

"Ummm.....yes." Cas tentatively tightened his grip and started pumping his hand the way Dean was. It was... _different_. He had masturbated before so he was familiar with his own penis but Dean's felt very different in his hand despite looking much the same.

Slowly Cas relaxed into the rhythm Dean was setting but it took a great deal of effort to remember to move his hand when Dean's hand was pleasantly sliding over his penis. He'd occasionally find himself sitting back on his heels, eyes closed, hand stationary and wrapped around Dean as he enjoyed the way Dean's hand moved. Dean clearly had more experience doing this than he had.

Dean had three fingers sliding in and out of his hole when he glanced over and got distracted by Cas. Cas's chest was heaving, he had his eyes almost closed, eyelashes fluttering, his mouth was opening and closing like he was whispering something under his breath, and there was this....utterly at ease look on his face that Dean had never seen before. Cas just had no inhibitions about what he looked or sounded like during sex and it was...Dean shivered. "Oh fucking christ, you look hot. I gotta remember to watch next time."

"Hmmm?" Cas tilted his head up and opened his eyes to find Dean staring at him strangely. "What?"

"Umm....nothing." Dean felt himself blushing again. Fuck. Why did he say that? Just because Cas wanted to have sex with him once didn't mean he'd want to do it again. ...but what if Cas _did_ want to do it again? What if...what if this was a regular thing?

Cas's eyes squeezed closed as he felt that odd telltale sensation in his groin. It was like everything was pulling together. He set his free hand on Dean's wrist. "Dean, I'm very close to achieving an orgasm."

Dean let go of Cas's dick. He didn't want the party to be over before it even started, especially if this was the only party Dean was ever invited to. "Dude, you can just say coming or if you want to be classy about it I guess you can say climaxing."

"Climaxing?" Cas had heard Dean use the term coming before and he didn't like it. Coming? Coming where? It sounded silly to Cas. But climaxing? That sounded more appropriate for how it felt when he had an orgasm. "Right. I'm near to having a climactic moment."

Dean shook his head grinning. Leave it to Cas to make coming sound awkward– and dear god he wouldn't give that up for anything. He jammed his fingers back inside himself testing out the stretch and slide. Everything felt good. He eyed Cas's dick and pushed his fingers in a little further. Yeah, that felt about right. "Alright. Lets do this."

**Notes for the Chapter:**

> Hahaha! You thought this was going to be **The Sex** , didn't you? Nope. But we shall get there in the next chapter.


	4. The Climactic Moment

**Summary for the Chapter:**

> Cas glanced down at Dean. He gingerly set a hand on Dean's back. Dean felt warm under his hand. The skin on Dean's back was surprisingly soft. He spread his fingers wide and slid his hand up, following Dean's spine. Dean took in a sharp breath. He yanked his hand away.

**Notes for the Chapter:**

> And here's the terrible mood ruining first time sex that I promised.

"Alright. Lets do this."

Neither of them moved.

Cas shifted uncomfortably as Dean stared at him. As the moment dragged on Cas wondered if this was how other people felt when he stared. Why wasn't Dean doing anything? Was he supposed to do something first? "....how?"

A look of abject horror sprung up on Dean's face. Cas rolled his eyes. He may be inexperienced but he was still significantly more knowledgeable on the subject than most humans. "I don't mean _how_. I mean....what way?"

"Thank god." Dean muttered under his breath. If Cas hadn't known what to do at all that would have been it. Dean would have called the whole damn thing off right there because there was no way he was going to explain how a dick worked to a virgin after they had been drinking all night.

"Okay...ummm....why don't...." Dean looked Cas over...yeah...how was a good question. Wow, he had not thought this out. Alright, what would be the easiest for Cas? He pressed his lips together thinking. He turned around. He shuffled back on his knees until he felt Cas's dick bump into him then dropped down to his hands and knees. "You got a good idea of how to do this?"

"I think so..." Cas wasn't sure if he'd say his knowledge of the subject was _good_ so much as detailed. He could tell Dean the rate of blood flow through a penis when erect, the chemical make up of semen, and the number of nerve endings associated with the anus. He had an _idea_ of how to do this but was it good?

Cas eased his hips forward experimentally. He pressed against Dean, pushing a little harder, and suddenly his penis slipped up sliding across Dean's butt. He jerked back with a hiss.

"You okay?" Dean had felt the slip and slid moment. It didn't feel like it would have hurt Cas but it didn't hurt to be careful. "Nothing...bent funny?"

"I'm fine. I just need...a moment to collect myself." Cas closed his eyes and breathed calmly. That pulled tight feeling in his groin and had threatened to release. "You're much better at manual sex than I am."

Dean found himself laughing quietly on all fours in front of Cas– which only made him laugh harder. Cas was complimenting his ability to give a hand job while he was waiting around with his ass in the air. "Yeah, well when your only consistent girlfriend is Palmela Handerson or her sister you gotta be good."

Cas frowned, "Dean. What are you _talking_ about? Who's Palmela?"

"Jealous?" Dean laughed.

"No. I don't even know this Palmela Handerson. Or her sister. How can I be jealous of them?" Cas ran over a list of hunters that he knew Dean associated with and were still alive. There was one named Shauna Henderson but as far as he knew she didn't have a sister and he didn't think Dean knew her well enough to refer to her as a girlfriend.

Dean couldn't help it, "I dunno, Cas. You were getting pretty friendly with Palmela earlier."

"What?" Cas narrowed his eyes. Had he drank so much he was forgetting parts of the night? That was worrisome.

Dean cracked up at how serious Cas sounded. He held his hand up, "Dude, relax. It's a joke name for the hand you jerk off with. **Palm** ela **Hand** erson."

Cas let out an annoyed huff. _Puns_. He rolled his eyes. At least it wasn't another baseball metaphor. He took a few more deep breaths as he waited for that too tight feeling to pass. He wanted to actually experience sex. Not just have an orgasm. He could do that on his own.

Cas glanced down at Dean. He gingerly set a hand on Dean's back. Dean felt warm under his hand. The skin on Dean's back was surprisingly soft. He spread his fingers wide and slid his hand up, following Dean's spine. Dean took in a sharp breath. He yanked his hand away.

"No. No, you can do that. It...it feels good." Dean encouraged. A moment later he felt that ghost of a touch over his spine again. He shivered as his skin crawled– in a good way. Definitely good. It had a sort of pleasurable pins and needles feel to it. He wondered how much of that was Cas and how much of it was the whiskey.

Cas swept his hand up and down his back, _barely_ touching. It still felt good but...more would be better. Dean reached back and caught Cas's hand near his hip. Dean pressed it down against his skin. "Cas, I'm not that delicate. You can grab on a little...if you want. I'm not gonna break."

"Alright." Cas tightened his grip where Dean had pressed his hand down. "Is that okay?"

"It's good." It was still a little on the gentle side but Dean wasn't about to introduce Cas to the kinky side of sex on his first go.

Cas let out a last deep breath and decided he was sufficiently calm. Time to try again. He leaned forward again, this time taking hold of his penis to guide it. Dean pushed back against him. It was all very strange. He could feel the latex wrapped around him but he could feel Dean pushing against him and he— **_Oh._** His fingers dug into Dean's flesh where he still held on. He glanced down. Part of the head of his penis had—

Dean pushed back a little more. It was weird, he could feel it when the head of Cas's dick was all the way in; his butt closing up after the flare of the head of Cas's dick. It hadn't occurred to him that he'd actually be able to _feel_ that. Everything had been stretching wider and then suddenly, _pop_ , and his butt had dick it in. Huh. The chicks that had pegged him had used pretty plain dildos on him, just a straight up hunk of silicone without much shape. He leaned away from Cas a little bit. Yeah. He could feel it. Every time he leaned away his butt actually had to stretch just a  _little_ bit wider to let the flared part of Cas's dick out. Huh. This was...actually a lot better than a strap on.

The silence in the room finally got to Dean. He bent his head over his shoulder, "You okay?"

Cas flicked his eyes up. Was he okay? Probably but he didn't know how to explain it. Cas opted for nodding instead. He pushed a little more of his penis in and stopped to shiver. If Dean had explained the way his penis would be squeezed tight inside something unbelievably warm and said that it was _enjoyable_ Cas would have thought he was making it up. He had squeezed his penis too tight while masturbating before, it hurt. And he had spilt hot soup on his lap before, that hurt too. But this was too tight and too warm and it felt amazing.

"You look a little startled." Dean said because Cas looked more like a deer in the headlights than a guy who was about to get laid.

"I'm fine. It's—" Cas hissed when Dean pushed back a little more. " ** _Ahh_**...it's.... _squeezing_....you're very warm."

Dean chuckled, "Hot and tight?"

"Yes." That did adequately described it. Cas breathed deep trying to keep his concentration.

"Awesome." Dean decided that he was going to take that as a compliment. He'd definitely wanted his ass to be described as hot and tight rather then loose and sloppy. He started laughing again. He really should have drank less.

"What're you laughing about now?" Cas could feel the vibrations of Dean laughing all around his penis.

"Nothing, nothing." Dean shook his head and grinned at the sheets on the bed. He _really_ should have drank less. Hot and tight wasn't funny and neither was loose and sloppy. He was about to tell Cas to keep going when Cas suddenly decided to just shove it in. His eyes went wide and his mouth dropped open as pain spiked through him. He flinched away, " **Whoa!** _Fuck!_ Hold on a sec!"

"I'm _sorry!"_ Cas pulled out and leaned around closer to Dean's face. All the fast movement sent him a spinning reminder that he had been drinking all night. He pressed his eyes shut for a moment until the spinning stopped then set a hand on Dean's shoulder. "Are you okay?"

"Yeah. Yeah, I'm fine." Dean took a moment to breath. Jesus christ, that had fucking hurt like a bitch. He dug around in the sheets and found the lube again. They had probably done too much screwing around before actually screwing around. He had clenched up again and the lube on Cas had probably dried up a little or rubbed off. No big deal - unless you were on the receiving end - he could fix this.

"Do you want to stop?" Cas asked. He wanted to have sex, not hurt Dean. He **_liked_** Dean after all. There were plenty of other kinds of sex they could have. Sex that wouldn't require so much work. Well, he didn't think it would require as much work. But then, he hadn't thought _this_ would require that much work.

"Nah. I'm good as long as you're still up for it." Dean squirted some lube onto his fingers and reached around to press it into himself. Cold lube normally sucked but the faint after burn of too much dick at once was making cold lube feel like a great idea. Things felt a little... _tender_ back there but it didn't **_hurt_**. So that was good. He hoped.

Dean hadn't sounded fine. Cas was sure that had been genuine pain. He studied Dean's face. "You're sure?"

"Yeah. Just let me set the pace for now, okay? You just tell me if you want to stop." Dean took his fingers out of himself and looked them over. He let out a breath of relief. There wasn't any blood or anything. Cas hadn't done any real damage. He'd just surprised the shit out of him– heh, pun not intended. Everything was okay. It didn't even really hurt anymore.

Dean lubed Cas up again, wiped his hand off on some blankets - he'd regret that tomorrow - then waited for Cas to get everything lined up to go again. He eased back. _Slowly_. There was that funny popping in sensation again as his butt wrapped around the head of Cas's dick and the stretching feeling as he pushed himself back. He stopped and started a few times to adjust and once when Cas had dug his fingers into his thigh and hissed _stop_ and then suddenly his butt was against Cas's hips.

Cas's chest was heaving as he sucked in air trying to maintain some semblance of control. Dean's description of hot and tight did **_not_** adequately describe this. Dean pulled forward a little then slid back. A million fiery sparks of pleasure sung through him from his groin to the base of his skull. Dean pulled forward a little more and slid back a little harder, bumping the curve of his butt against him. He whimpered out a soft _Ahh!_ as those sparks zipped through him again. And again. And again.

Very slowly - _too slowly_ \- Dean began moving at a faster pace. Cas set his hands on Dean's back and slid them down to Dean's hips. He could feel the muscles beneath his hand flex and twist. Every time Dean pulled away Cas wanted to pull him back - to keep that squeezing warmth around him - but fear of hurting Dean again kept him still. He leaned forward a little when Dean started to let him slid almost all the way out. It made Dean's butt bounce off his hips. He gasped at the impact. If Dean kept this up he was going to climax _very_ soon. He could already feel that tightness building up in his groin again.

Dean craned his head over his shoulder for a glimpse of Cas but it was harder than he thought it'd be to look and keep fucking himself back on Cas. Dean really wished he had a mirror set up like that one chick had done up in her room. A few well placed mirrors and he could be watching Cas.

Cas made a noise. Dean jerked his head around again to see if it had been a good noise or a bad noise. What was Cas doing? Did he like it? Was he freaking out? What the hell was going on back there? There were a few more panicky **_Ahhs!_** Dean craned his head over his shoulder again. What was Cas **_doing_** _?_ He couldn't get a good look. He let out a low growl. This was fucking stupid. "Okay. We gotta change this up."

Cas nodded and breathed out one word, " _Okay_."

Another long _Ahh!_ escaped him as Dean drew away and his penis slid out. Cas sat back on his heels, knees spread as far apart as they would go so nothing touched. He could feel the phantom press of Dean all around him still. The bunker air, which was usually a comfortable temperature, felt cool against him. He sighed. That coolness felt wonderful. He shivered as his own breath brushed against his skin, even that was too much contact. He leaned his head back. He let his hands fall to the bed. He clutched at the blankets and held on. He just needed to hold on to something for a moment. Just for a moment.

Dean leaned away until he felt Cas pop out then turned around. Cas had his head titled back, the long line of his neck was slick with sweat, he was breathing hard, and his legs were spread wide and....and...holy mother of god, _Cas looked like **sex**_. He gaped at Cas until Cas rolled his head forward to look at him. Oh, that did not help. Cas had a case of sex hair to end all sex hair.

"What?" Cas wasn't sure why Dean was staring at him like that. Dean looked like he was surprised and afraid. Had he been that bad at sex? He frowned, "Did I do something wrong again?"

"No. No......keep– keep doing _that."_ Dean licked his lips and ran his eyes over Cas again. He rolled his shoulders and squirmed. _That_ had been fucking him? Holy fucking christ. How the fuck did a virgin look like that? ...how did a newly not-a-virgin look like that?

Cas tilted his head off to the side. What was Dean talking about? He wasn't doing anything. If he did do anything in the next few minutes it would likely be _have an orgasm_ because he was sure the slightest touch to his penis right now would finish the task.

Dean gulped and tried to ignore what was sitting in front of him. He had kept his promise, Cas wouldn't die a virgin, but it may have suddenly turned into Dean's mission in life to watch Cas come. He needed to figure out how to do that _now_.

Dean took in another not so subtle look at Cas. Well, he definitely wasn't going to get Cas to lay down and so he could ride him. Cas would look fucking hot and he'd just look like an idiot bouncing around on top. Laying out on his stomach would have the same problem as doing it doggy style. From the side maybe? He thought about how that would feel and wrinkled his nose. Okay, so...missionary? Could he even bend his legs enough to do that?

Dean laid out on his back and spread his legs open. He waved Cas over. Cas paused for a moment beside him before blinking rapidly a few times then awkwardly crab stepping on his knees and settling between Dean's legs. Dean ran his hands along Cas's sides and pulled him down. Cas leaned over him, a hand to either side of Dean's head. Dean grinned, "Hi Cas."

"Hello Dean." Cas carefully kept his hips away from Dean. He wanted to climax _with_ Dean, not over top of him.

Dean chuckled at Cas's too solemn face. That wouldn't do. He ran his hand up the back on Cas's neck and into his hair and pulled him in closer to kiss. Yeah. This way would be awesome. He could watch _and_ touch.

Cas whimpered as Dean kissed him. Dean was rubbing one hand up and down his side. Dean's other hand pulled at his hair... _and it felt good_. He hadn't really believed that— His back arched when Dean raked his nails down his back. He flung himself away. _Too much. Too much. Too much._ He was going to end up climaxing without Dean.

"Shit. Sorry. I- I got- Cas, you okay? I didn't break the skin or something did I?" Dean sat up and started tugging at Cas to check out his back but Cas kept pulling away. Oh fuck. He had ruined it. This was going to be what Cas thought of for the rest of his life when he thought of sex. Crappy painful sex with him. Fuck.

" _I'm fine."_ Cas hissed and tried to squirm away again. Dean's leg kept rubbing up against his penis as he grabbed at him. He was going to orgasm before he wanted to and he wanted to do that _with Dean_ and he didn't think he'd get another chance at this rate because he was terrible at this. "Dean! I'm fine!"

Dean froze. Fuck. How was he screwing this up now? "...you're fine?"

" _Yes."_ Cas took a relieved breath. Dean had leaned away. There was no more maddening touch against his penis. He closed his eyes and took another breath. "I'm fine."

"...then what he hell was all that about?" Dean didn't believe it. No one fought to get away like that if everything was fine.

"I was going to climax." Cas said, eyes still closed. How did humans stay calm long enough to procreate? Maybe it was just him. Premature ejaculation was a fairly common problem. It would be statistically reasonable that the body he had inherited was predisposed to it.

"Oh." That wasn't what Dean expected at all. He blinked. Had Cas.... "You liked it? When I scratched you."

"Yes."

Dean rubbed at his neck. Cas had liked it but didn't want to get off? Why didn't Cas want to get off with him? "Then why...why didn't you just do it?"

"Do what?"

"Come."

Dean almost sounded hurt. Cas opened his eyes. Dean looked...betrayed? He really was terrible at this. Maybe he shouldn't have asked to have sex after all. His logic on the couch had been fuzzy at best. "I want to climax _with_ you." Cas frowned. That wasn't just it. Yes, he wanted to climax _with Dean_ but he wanted... "I...I want you to like it too."

Dean started to laugh again. Cas rolled his eyes. Why was it funny that he wanted Dean to like this? Most humans wanted their sexual partners to like it. Dean routinely bragged about how much his sexual partners had enjoyed themselves. Was he so terrible at this it was laughable to think someone would enjoy sex with him? He shuffled over to the edge of the bed. Sex was a terrible idea. He'd just go back to drinking instead of giving Dean unsatisfying sex.

"Hey, where do you think you're going?" Dean grabbed Cas's shoulder and hauled him back into bed.

"To drink. I'm terrible at this." Cas said dejectedly.

Oh, wow, did he ever feel like an asshole for laughing again. Dean brushed his hand along Cas's face. "You're not terrible at this. I'm just an idiot and drank too much. You're actually pretty good at this for your first time."

"...really?" Cas was suspicious Dean was just trying to placate him.

"Yeah really." Dean tilted Cas's chin up and leaned in to kiss him again. He made a mental promise to himself to quit fucking laughing. This was Cas's first time he didn't want him to get some weird sex hang-up because of him. "You still want to do this? I promise I'll try to stop being a dick about it."

Cas hesitated before slowly nodding. He let Dean draw him back to the middle of the bed.

Dean grabbed the lube again because too much was not a bad thing. He was about to put more on Cas but stopped. "You're not still gonna go off like-" Dean snapped his fingers, "-that?"

Cas reached for the bottle of lube. "Let me do it."

Dean watched Cas carefully spread lube on his dick. He glanced down to see what was going on with his own neglected cock. Things were not looking as perky down there as he wanted them to. He wrapped his fingers around his cock and started pumping. He didn't need to imagine anything to get himself good and hard again, he just had to watch Cas.

Cas finished spreading the lube on and looked up to see Dean stroking himself. The memory of how Dean's hand felt on him made his breath hitch. _Dean was doing **that** to himself._ Dean gave a little twitch when he noticed him staring. A sly smile crept up on Dean's face. Cas watched him lay back, his strokes turning long and languid. With the other hand Dean motioned for him to come closer. Cas crawled back to where he had been before; between Dean's legs and leaning over top of him. Dean smiled at him again. Cas bent down to kiss him. This felt more like what he had imagined sex to be like; less too hot and too tight and more warm and soft. ...though too hot and too tight had felt _very_ nice. Then Dean started moving. He eased back from the kiss.

"Okay, bear with me for a sec." Dean squirmed around under Cas. He flexed his hips up and rolled them out. He tried hiking his knees up. He tried wrapping his legs around Cas. He attempted to get one hooked over Cas's shoulder and discovered he was definitely not that flexible. Fuck. He let his legs fall back to the bed. _Fuck_.

"Here." Cas sat back, running his hands over Dean. Dean's skin shivered underneath his fingers. Cas liked that and from the way Dean breathed Cas suspected Dean liked it too. He gripped tight onto Dean's hips. He was fairly certain he could practically apply some of that detailed knowledge he had.

Dean let out a soft yelp of surprise when Cas grabbed his hips and angled them up. Dean felt Cas scooch forward and get his knees under Dean's legs– and suddenly his legs were bent and more naturally fit around Cas. Huh. Where the hell had Cas picked that up? Then Cas started to push his dick back in, slowly leaning in with it. Dean forced himself to relax. Cas slotted his hand under Dean's knees and pushed them back and apart, falling gently forward with them. When had Cas figured all this out?

Cas wanted **_in_**. He wanted to push in quick and revel in that too warm and too tight feeling but that hadn't worked last time. That had hurt Dean. So he willed himself to sink in bit by bit. Those millions of little sparks racing up and down his spine as he did making him shake and groan.

Dean watched Cas's face flick between a million different emotions until finally Cas was leaning over him while he was bent up like a pretzel with a dick in his ass. Pretty great night overall.

"You okay?" Dean asked. Cas had that deer in the headlights look again.

"Yes." Cas closed his eyes and held still as he waited for the rush of pleasure of being **_in_** to settle down. He let Dean's legs go and a moment later felt them wrapping around him and pressing him in a bit closer. Now he had to wait for a new blast of pleasure to subside before he could do anything.

When he was sure he was back in control Cas rocked his hips down. He stopped. He shivered. He wasn't in control. He closed his eyes and breathed deep and harsh and tried again. Moving this slowly was agonizing; every nerve ending flared up with pleasure and burned into him.

Dean set a hand on Cas's neck to get his attention. Cas's eyes popped open. Dean slid his hand up to Cas's face. "You can go faster."

Cas hook his head, "I hurt you last time."

"Yeah, because we had barely even gotten going then. Trust me Cas, we've been going at this long enough. You can go faster... _if you want_. I can take it." Dean said. Actually the thought of Cas going to town on his ass had him aching just thinking about it but this was about Cas. If Cas wanted to go slow, they'd go slow.

Cas studied Dean's face for any misgivings. He didn't find any. He snapped his hips into Dean twice. Dean slammed his eyes shut and his head jerked back as he made a high pitched noise. Cas stopped mid thrust. He had hurt Dean again.

Dean's eyes flew open. Cas was staring down at him concerned. _Why?_ That had felt fucking awesome. "Why'd you stop?"

Cas stared down surprised. Dean didn't sound hurt. He tilted his head off to one side, "You're okay?"

"Yeah, I'm okay." Dean grinned and ran a hand down Cas's back, gently scratching. Cas shivered as his eyes flicked over him. Dean tightened his legs around Cas and pulled him closer, trying to get him started up again. Cas nodded thoughtfully and suddenly Dean got exactly what he wanted. "Oh fuck! Holy– _Ahh!_ Fuck! Cas!"

Cas thrust in to a litany of _oh fucks!,_ gasps, and his name. The faster he moved the faster words spilled from Dean's mouth. Those sparks of pleasure weren't slowly burning their way into him anymore or racing up and down his spine. They were snapping at his very core clawing their way through him.

It all snuck up on Cas. He didn't notice when that tight feeling in his groin started again but he did notice when he had gone too far to stop it. His heart picked up. His mouth dropped open as he heaved in breath after breath. Somewhere it registered that he was making a noise deep in his throat but that sensation was nothing compared to the way everything was drawing together. Coiling tight. Just waiting for that last needed touch to release. Dean's nails dug in and tore down his back. Cas arched his back. His hips slammed forward. The world narrowed down to nothing but chasing after the pleasure that raced through him as that tightness finally released.

Dean watched as Cas lost it. He watched Cas look surprised, then far too serious, and finally content; jack-rabbiting into him the whole time. Goddamn. He really hoped Cas wanted to do this again sometime. Cas collapsed against him, twitching and groaning. Dean wrapped his arms around him. Cas was crushing the air out of his lungs but Dean didn't care. He rubbed his face into Cas's hair and breathed deep. A happy little bubble of warmth sprung up in his chest. Fuck. .... _fuck_. Fuck, it was just sex. Cas just wanted to know what sex was like. He had no business feeling sappy about it.

Cas pressed his face into Dean's shoulder and breathed deep. The scent of Dean calming him down, taking the edge off the rawness of his nerves after climaxing. "Can we do this again?"

That was probably a terrible idea if Dean was going to feel all sappy about it. Dean squeezed his arms tighter around Cas. "Uh huh."

Cas shifted between Dean's legs. Something hard pressed against his stomach. He pushed himself up off Dean and looked down. He frowned. Dean hadn't liked this after all. "You didn't...I'm sorry I'm not good at this."

Dean flicked Cas's nose, "Hey, don't go getting all upset about it. You're gonna start giving _me_ hang-ups."

Cas's eyebrows came together. Dean could see him forming some kind of crazy ex-angel logic that would probably have Cas thinking he was terrible at sex for the rest of his life. Dean rolled his eyes. Holy crap, Cas. Can't give a guy a few minutes to appreciate a good post fucking cuddle? He grabbed Cas's arm and pulled at it until Cas shifted his weight and let him move it. He guided Cas's hand down and wrapped Cas's fingers around his dick. He set his own hand on top and started pumping until Cas caught on and did it on his own.

Dean relaxed back into the mattress. Cas watched his face go slack as he enjoyed himself. Maybe he was better at manual sex than he thought he was. Dean seemed to like it. He fell into a rhythm as he stroked Dean, wondering what it felt like for him. Then Dean started to rock his hips up into his hand. Every roll back down would make Dean hiss. Cas watched fascinated. Was Dean...? Cas experimentally thrust his hips. Dean gasped. Cas did it again. Dean breathed hard.

Cas shifted around so he could support himself on one hand and comfortably rock his hips into Dean. He didn't think he'd be able to do that much longer. He was still somewhat erect but he'd be too soft to do this soon. He pumped his hand faster and sped up his hips. Dean started to swear again. Cas took it as a good sign. Dean yanked his head down and started to kiss him. It was all very awkward to keep doing but he didn't have to for much longer. Dean started breathing hard through the kiss and finally pulled away to throw his head back and arch his hips to thrust into Cas's hand. A moment later Cas's hand was warm and wet.

Dean took a deep breath and let it out with a loud huff. That had been one hell of a hand job. Why the hell did Cas think he was _bad_ at this? A little more practice and he'd be awesome...and Dean would totally help him practice if he wanted. He reached out and ran his hand through Cas's hair. "So how does not being a virgin anymore feel?"

Cas brought his hand up and rubbed his fingers together, "Sticky."

Dean snorted as he watched Cas study the come on his hand, "Yeah, sex will do that but hey, there's always crusty to look forward to later."

Cas frowned, "Why would you look forward to that?"

Dean shook his head. Lieutenant Literal. Dean let his legs fall to the side. His knees felt stiff. He definitely needed to stretch them out straight before they cramped up. He pat Cas's arm. "Okay, come on."

Dean motioned for Cas to move. He looked down at his stomach and grimaced. There was come everywhere. Cas definitely had not even tried to catch it. Dean wiped the come off his stomach with the sheet. He'd regret that later but he didn't care right now.

"...it came off."

Dean turned and looked at Cas. "What?"

"The condom." Cas motioned to his penis. "It came off."

"What do you mean, it came off?" Dean looked down at Cas's dick. Sure enough, no condom.

"I mean it's no longer on my penis. What do you think I mean?" Sometimes Cas wondered about Dean's grasp of the English language.

Dean stared at Cas's dick. "....where the hell is it?"

Cas shrugged.

They felt around in the bed for a few moments - Cas found one of the condoms he had messed up putting on - before Dean came to the more logical conclusion of where the used condom was. He rubbed the heels of his palms against his eyes. "Ugh. Why me?"

"What?" Cas asked.

"Nothing. Just grab the box of kleenex." Dean said as he bent around and started to try and fish a used condom out of his ass. Ugh. Fuck, this was gross. And it was entirely his own fault. He should have told Cas to pull out when he was done. Not let him keep fucking him while getting a hand job....it _had_ been a pretty good hand job though. It didn't take long before he felt it. He hooked a finger on it and pulled it out, along with a mess of come and lube. **_Ugh!_** He held the condom up. Well... _some_ of Cas's jizz was still in there. At least it wasn't as gross as it could have been. It could have been covered in...well, _the obvious._ He really hadn't planned tonight out very well. Whatever, shit happened. Dean burst out in another fit of giggles because in this case, shit had not happened.

Cas offered the box of tissues looking confused. Why was Dean laughing again? He had looked rather upset about the condom a moment ago.

Dean grabbed a couple kleenexes and wadded the condom up in them. He tossed it towards the trashcan but his fingers were sticky with lube- _and come_. It stuck to him and fell to the bed. He looked around in the folds of the blankets for it but couldn't find it. He threw his hands up, "Fuck it. Most of it is on me anyway."

Cas offered him the box of kleenex again. Dean grabbed a few more and tried to clean himself off the best he could. It was mostly just a big mess of lube.

Cas clutched at the box of tissues as he watched Dean wipe himself off. What should he do now? When Dean had sex it was generally for one night and he left soon after but he was in Dean's room. Should he go? He looked over his shoulder at the door. He didn't want to go. He wanted to stay. But what if Dean didn't want him to stay? All he had asked Dean for was sex. They had had sex. He hadn't... _asked about anything else_. He looked back to Dean. What was he supposed to do? "....now what?"

"What do you mean, now what?" Dean asked looking over a particularly sloppy kleenex and grimacing. He threw it on the floor. He had given up on aiming for the trashcan. Add a bunch of lubed-up-come-covered kleenexes all over his floor to the list of things he was going to regret tomorrow. He realized Cas hadn't said anything back. He snapped his head up. Cas looked worried. Why the hell was Cas worried? He wasn't really that mad about the condom thing. It was just gross. He set the box of kleenex down. "Cas...? You still okay, buddy?"

Cas looked away from Dean. How was he supposed to ask about...about _staying?_ He glanced at the door.

Dean rolled his eyes; as if he'd kick Cas out after. He grabbed Cas's arm dragged him down to the bed. He rolled over and turned off the lamp. He reached out for Cas in the dark. Cas shivered under his touch. He pulled at him as he squirmed closer. "Come here."

Cas gladly obeyed. He wriggled backwards towards Dean as Dean curled up around him. Dean had been right about the crusty part. He could feel the dried semen on Dean's stomach against his back. He didn't care. He pressed his back harder against Dean. He sighed as the heat from Dean's body sunk into him.

Dean pulled Cas's butt into his lap and bent his legs up under Cas's legs. He wriggled around until his dick was wedged between Cas's butt cheeks. He snaked an arm around Cas and made sure he was pulled in as tightly as humanly possible. This was probably the best way imaginable to fall asleep.

Dean was almost asleep when Cas broke the dark silence around them.

"Dean?"

"Yeah?"

"I like this as much as sex."

"Me too."

"Can we....can we do this part again tomorrow night?"

"Sure."

"...without sex first?"

"Yeah....yeah we can do this part again....however many times you want."

"I'd _like_ that."

"Good. Me too."

"Dean?"

"Yeah?"

"I think I found the condom."

Dean burst out in laughter against the back of Cas's neck.

**Notes for the Chapter:**

> I guess this is my way of saying that not everyone's first time has to be a raging success you'd want to write home about.


	5. Liquid peeps

**Summary for the Chapter:**

> Sam set the glass of water down in front of Cas then sat down across from the hangover victims. Jeez Cas looked horrible. He leaned forward. "You okay, Cas? You look kinda green."

Sam had been feeling vindictive when he had first got up to go out jogging. He had barely slept at all last night. Every time he thought he was about to get some peace and quiet he'd hear some new horror coming from Dean's bedroom. So he had made sure to slam a few doors and knock some things over on his way out. He worked out an entire list of demands as he jogged. First, he'd make Dean clean up everything. There were clothes all over the place and the two idiots had knocked a bunch of things over and he wasn't even going to ask why his shampoo was all over the bathroom but he was _not_ going to be the one to clean it up. Then he was going to make Dean's favourite breakfast and eat it in front of him. That was where his plan started to fall apart.

If it had been any other guy Sam would have gleefully poked fun at Dean's years of denial that he liked men too. He would have happily brought it up every chance he got just to watch Dean turn red. But no, Dean had to go and sleep with Cas. And that meant either everything was going to be sunshine and rainbows and maybe Lebanon would have to start throwing pride parades or it meant Dean was going to take off from the bunker for weeks and Cas would probably think it was all his fault and try to leave too. Then _he'd_ have to go drive around the country looking for the two idiots because his brother was a knob and Cas was....well, Cas was Cas.

The whole problem with his plan came down to the simple fact that he felt bad for Cas. Not just because for some reason he liked Dean - really Sam felt sorry for anyone that had to deal with Winchester emotional baggage - but because what happened in the next couple of hours was probably going to be entirely out of Cas's control. Dean was either going to be okay with what had happened or he was going to freak out. So if he harassed Dean about it and Dean got defensive...well, then it'd be all his fault that Cas was moping around the bunker while Dean fucked off to who knows where.

He sighed. He'd be nice to Dean for Cas's sake.

\---

Dean woke up when something jabbed him in the chest. He felt around. His fingers hit something warm. He jerked his hand back. _What the fuck?_ He rolled over and turned his bedside lamp on. He looked back over at...Cas?

Oh...right. Cas. They had... ** _oh._** Okay. Wow. And Cas had asked to _stay_...Cas had asked to _come back_...Oh... _oh no_... Dean bolted out of bed and raced to the bathroom. He could feel that telltale heave starting. Fuck! Why did he pick a room so far from the bathroom!? He skidded into the bathroom and slid through– Why _the fuck_ was there shampoo everywhere?

He nearly fell flat on his ass as he slipped in the shampoo but he made it to the toilet in time to throw up. Why the fuck had he drank that much?

When his stomach finally stopped heaving he flopped back against the wall. Bad idea. His head fucking killed, his back hurt from throwing up, and his butt was tender. He sniffed the air. And he smelt like a booze soaked gym sock some teenage kid had been jerking off into. He looked down himself. Ugh. And he was just as crusty as one too. He hauled himself up and slipped in Sam's stupid fruity smelling shampoo again. What the hell had Sam been doing in the bathroom? He grabbed some used towels from the laundry hamper and wiped up the shampoo, shaking his head and swearing under his breath the whole time.

Satisfied that the bathroom was clean enough, he grabbed a clean towel and headed for the shower grumbling all the while about how _nobody_ else cleaned up around the goddamned bunker. Why did he have to clean _everything?_

He scrubbed himself down in the shower, careful to avoid two sets of finger shaped bruises on his hips, then headed back to his bedroom. Where Cas was.

\---

Cas woke up alone and in Dean's room. He sat up and looked the bed over. They had had sex. He knew that. He just didn't remember _why_ exactly. What had he said to Dean that had made them come here? Had he told Dean how he felt? Where had Dean gone since then? Oh....

His fingers curled into the sheets. Dean always left after sex.

Cas startled when he heard Dean's voice from the doorway.

"You look like shit."

Dean's voice set off a sharp shooting pain through his head. Cas pressed his fingers to his temples and rubbed as he watched Dean come closer to him wearing nothing but a towel and carrying another one in his hands.

Dean tossed the towel he had grabbed on the way out of the bathroom onto the bed beside Cas. "Go shower. You'll feel better."

Cas stared up at Dean. What did that mean? Was Dean telling him to get out of his room? Or was he just telling him he'd feel better if he showered? Cas stared up at Dean and didn't get an answer. He dropped his gaze to the floor. Either way he needed to dress. He looked around for his clothes but didn't see them anywhere.

Dean saw Cas looking around and figured he was probably wondering the same thing about the clothes situation. "Yeah. I don't know. I guess we stripped down in the living room?"

"Oh." Cas waited to see if Dean was going to say anything else. He didn't. Cas stood up and wrapped the towel Dean had given him around his waist. He walked past Dean hoping for... _something_ but nothing happened. He lingered at the door for a moment but Dean had his back to him as he picked up tissues off the floor. Cas's shoulders sank. He turned and left Dean's room.

Cas felt cold and sick as he walked to the bathroom. He knew most of it was from a night of heavy drinking but some of it, especially that weight in the pit of his stomach, was from being sent away by Dean.

The bathroom smelled strongly of Sam's shampoo when he got there. Sam must have showered earlier. Cas made his way to the shower and turned it on. He stepped into the hot spray of water, careful to keep his aching head out of it, and stood numbly staring at the soap and shampoo on the ledge. There was an assortment of products from the various people - friends - who were living in the bunker. The only person not to have their own things on the ledge was himself. Dean had told him he could use his when he had first come to the bunker. Cas didn't want to use Dean's things. He didn't want to smell like Dean after being sent away.

Cas grabbed Sam's shampoo and Kevin's soap. He didn't think they'd mind. He scrubbed at his skin until it turned pink and washed his hair twice- it was surprisingly greasy. He rinsed off and stepped out of the shower to find Dean sitting on the bathroom counter picking at a loose thread on his robe, swinging his feet back and forth.

Dean glanced up when he heard the shower turn off. Cas was staring at him like he was considering murder. Whoa. What the hell had _he_ done? He reached over to the clothes beside him and offered them to Cas. "I...I thought you might want some clothes..."

Cas felt his face soften. Maybe...maybe he _had_ told Dean everything last night and now Dean... Sam had told him that Dean didn't understand how to _'do emotions'_ and Charlie had told him that Dean was more comfortable with _'little L's'_ rather than _'big L's'_. Maybe this was how Dean _'did emotions'_ after sex. Maybe Dean wasn't comfortable with _' **any**_ _L's'_.

Cas took the clothes. They were another pair of sweat pants and a t-shirt Dean had given him. It occurred to Cas that he really didn't own much of anything that hadn't been Dean's before. Maybe that was Dean's way of telling him that...that he... _liked_ him too.

Dean watched Cas get dress - the dude look considerable less smitey with pajamas on - then slid off the counter and nodded towards the door. "Come on, I think Sam's making breakfast."

\---

Sam was flipping the bacon when he heard a moan from behind him. He turned to see Dean in his dead guy robe blinking at the light in the kitchen.

"Coffee?" Dean asked squinting at the light. He put a hand up to shield his eyes. "Ugh, fuck me, why are the lights so bright in the bunker?"

"Because humans are only capable of seeing a very narrow range of radiation." Cas said, shuffling in behind Dean holding his head.

Sam laughed at Cas's answer which got a glare from both of them. He pointed over to the coffee pot. Dean made an appreciative noise. Cas stared blankly. Cas looked _horrible_. Holy crap. What had Dean done to the poor guy last night? Wait. He didn't want to know that. He pointed over to an assortment of bottles on the counter that he'd preemptively collected for Cas– Dean could suffer on his own. "There's some Advil if you want it, Cas."

Cas made a low noise in his throat. Advil. Yes. That was a good idea. He picked up the bottle and fought with the childproof lock while Dean looked over the remaining assortment of medication Sam had set out and started opening bottles.

Dean watched Cas suffer through the clicking noise the stupid safety cap made; torture for anyone with a headache, himself included. He put his hand out. "Here. Let me do it."

Cas passed the bottle over. Dean had it open on the first try. Dean passed the bottle back. Cas took it and squinted at the dose recommendations. He poured two tablets out. Dean passed him a glass of water. He put the tablets in his mouth and drank them down with the water then watched Dean take two tablets but use a disgustingly pink liquid medication to wash them down.

Dean arched an eyebrow at the way Cas was staring at him looking confused and little like he had gotten a whiff of some rotting garbage. Dean sniffed at himself. It wasn't him despite what he had smelt like earlier. He put a hand on Cas's lower back and pushed him along to the table. Huh. Now he was smelling something weird. What was that? He sniffed at the air...was that...Cas?

Sam fixed up three plates of bacon, eggs, and toast and set them down on the table while the zombies got themselves sorted out. He cleaned up and got some water for Cas because he wasn't sure if Cas was going to be able to make it to the sink if he got up. At least that was the worst of Cas's problems so far. Dean seemed to be taking things well. Sam glanced over at his brother. Dean was sitting at the table beside Cas staring vaguely off into the distance. Okay, so maybe Dean was still drunk.

Sam set the glass of water down in front of Cas then sat down across from the hangover victims. Jeez Cas looked horrible. He leaned forward. "You okay, Cas? You look kinda green."

Cas thought the question over. The feeling in his stomach he had thought was rejection _wasn't_ rejection. "...I think I'm going to be sick."

Sam darted up and grabbed the trashcan. He flung it down beside Cas. No way was he cleaning up after Dean today _and_ a bunch of puke off the kitchen floor.

Dean pulled Cas out from the table, still in his chair, and shoved his head over the trashcan. Cas heaved a few times. Dean rubbed his back. Fuck. They shouldn't have drank that much last night. What if Cas cracked a rib from throwing up? It could happen. Sam had done it once.

Sam grabbed the pepto-bismol and paper towel off the counter. He tore off a few paper towels and handed them to Cas. Cas looked like he was ready for someone to kill him and end his misery. He picked up the glass of water on the table and offered it to Cas. "Just swish it around in your mouth and spit it in the garbage can the first time. Trust me."

Sam was right, that first gulp of water was disgusting. Cas spit it out. He sat with his head over the trashcan while Dean rubbed his back. He would have liked to take comfort in that but his head was throbbing and he was fairly certain he had thrown up the Advil.

Dean watched Cas blow chunks and rubbed his back - and Cas _did_ smell weird - and felt guilty about the whole damn thing. Cas wouldn't be throwing up and feeling like shit if he hadn't talked him into getting wasted last night.

Sam poured out some pepto-bismol and offered it to Cas. "It looks like liquid peeps but it'll help."

Cas didn't know what peeps were but he took one look and threw up again. It was awful. Why did people drink if this was the result? He'd felt sore as an angel when he drank but he hadn't felt like...like **_this_**. When his stomach finished heaving he took the pink medication Sam was holding out. He had to close his eyes while he drank it. The colour was disconcerting.

When Cas looked a little less green around the gills Dean pushed Cas's plate a little closer to him. "You should eat something. It'll help settle your stomach."

"Yeah. You really should." Sam agreed.

For a moment Cas had thought Dean's suggest was one of the ridiculous things he had been trying to convince him of since becoming human but Sam had agreed. It still sounded like a terrible idea. "No. I feel horrible."

Dean nudged the plate a little. "Come on, Cas."

"No."

"You're just going to keep feeling like shit if you don't eat something." Dean picked up a piece of bacon, waved it under Cas's nose, and poked it against Cas's lips.

Cas leaned away and glared at the bacon. "I'm going to throw it up."

Dean pulled his hand back slowly. That was not a happy Cas face. He jammed the bacon into his own mouth deciding he'd rather eat the bacon instead of getting his hand bitten off.

Sam shook his head at Dean. What was wrong with his brother? And why did Cas want to put up with that? He turned to Cas, "Just try something. You'll feel better."

Cas eyed Sam wondering why he was suddenly trying to help Dean play jokes on him.

Sam offered Cas a piece of plain toast, "This should be easy on your stomach."

Cas stared at it mournfully for a few moments before accepting the toast. Sam probably wasn't playing a joke on him. He sat quietly, taking small nibbles of toast and painfully swallowing them as he shivered.

Dean watched Cas shiver and quake in his seat looking like hell warmed over. Fuck. That was his fault wasn't it? He worked his robe off and settled it over Cas's shoulders. He frowned. What _the hell_ was that smell on Cas?

Cas jumped when he felt the robe drop down on him but let out a little sigh when he realized what it was. He wanted to deeply regret drinking last night but if he hadn't then Dean wouldn't be doing this. He closed his eyes relaxing into the warmth and the smell of Dean. His head slowly sunk down to the table.

Sam reached over and moved the glass of water out of the way before Cas knocked it over while he passed out. He shot Dean a look, _How could you?_

 _I didn't **make** him drink._ Dean scowled back.

Sam rolled his eyes, _Right_.

Dean glared, _This is your fault._

Sam shrugged at him and nodded at Cas, _How is this **my** fault? **You** slept with him._

Dean opened and closed his mouth a few times before snapping it shut. His eyes shot down to his plate as his face turned red. He stabbed at his eggs with his fork. He'd talk to Sam later.

Sam shook his head while the rest of him shook with silent laughter.

Fifteen minutes later Dean finished his breakfast– and most of Cas's. He gathered their plates and brought them over to the counter. He went back to Cas and gave his shoulder a squeeze, "Time to go back to bed."

Cas didn't budge. Dean gave Cas's shoulder another squeeze. Cas groaned but he started to pull himself up and blink like a confused owl.

Cas drew Dean's robe around his shoulders like a blanket and heaved himself out of the chair. Bed sounded like a wonderful idea. Especially the thought of having Dean curl up around him again. He felt cold and miserable, Dean felt warm and...and well he _liked_ Dean.

Dean hesitated looking between Sam and Cas. He needed to talk to Sam. He...he had to make sure things were... _cool_....with Sam. Right. As soon as Cas left he'd have it out with Sam. Then he'd crawl into bed too and pass the fuck out. His head snapped back to Cas. It had just occurred to him where Cas was probably going. Gross. He grabbed Cas's shoulder before he left the kitchen, "Hey Cas? Go to your room, okay?"


	6. A long time coming

**Summary for the Chapter:**

> Dean crossed his arms. What the hell was wrong with everyone?

**Notes for the Chapter:**

> It cracks me up that I can totally see Cas happily adopting some human figures of speech but not others. Big L vs little L to describe how Dean views talking about emotions? Sure. But call a penis a cock? What? Why? It's not a bird. Why would you call it that?

"Hey Cas? Go to your room, okay?"

Sam dropped the plate he was holding. It hit the counter with a clang. He turned slowly. Cas looked like he had been stabbed through the chest. Dean looked confused.

"What?" Dean jerked his head back and forth between Sam and Cas. Sam looked pissed and Cas...he didn't know what to call the look on Cas's face. Dean shrugged and threw his hands up defensively. "Why's everyone _looking_ at me like _that?"_

Cas took in a shaky breath. It really had just been sex to Dean. He shouldn't have presumed, even if Dean had said he was welcome back. It had been an answer given under the influence of alcohol. Humans made _notoriously_ bad decisions while drinking. _He_ had made bad decisions while drinking last night.

Sam swallowed hard. Fuck, and here was the fallout he had been expecting. Cas flinched when Dean's confusion shifted to annoyance. Cas looked like he was trying to lead a full scale retreat into last week while frozen to the spot. Great. Just great. Sam glared over at Dean waiting to hear what ridiculous excuse he was going to come up with.

Dean crossed his arms. What the hell was wrong with everyone? Why did Cas keep _looking_ at him like **that**? He knew Cas had asked to stay but he hadn't thought he meant stay specifically in _his_ room. It totally wasn't fair if Cas got to stay in his room and he didn't get to stay in Cas's room...and why was Cas _still_ looking at him like that?

"Dude, I am _not_ crawling back into my bed until I've washed those sheets. There is jizz and lube _everywhere_." Sure Dean wanted to curl up with Cas and sleep his hangover away but he had to draw the line _somewhere_ and jizz sheets was where the line started. "You can go sleep in there if you want but I'm sleeping off my hangover somewhere clean."

The stress went out of Sam's shoulders. Then immediately came back. Jizz and lube everywhere? He didn't need to know that.

Cas let out the breath he was holding. He had thought... He breathed deeply. He had thought Dean was telling him he wasn't welcome in his room again but Dean had only meant his bed wasn't clean. But...wait...Dean hadn't said he was coming to _his_ room to sleep, only that he shouldn't go to Dean's room because it wasn't clean. Maybe Dean _wasn't_ coming to his room.

Dean gave them both a funny look. He shook his head. Cas and Sam were weird. Why was he the only normal one? He made a shooing motion at Cas.

Cas stood his ground. He needed to know. He needed to hear it, "....you're....you're coming? ...to my room?"

"Right behind you." Dean could feel his face heating up again - he just _knew_ Sam was staring at him - as he pulled the edges of his robe tighter around Cas. Cas still looked like shit and it was his fault...maybe he'd make Cas soup later. ".....just gotta help Sam with the dishes first."

Cas nodded as a wave of relief swept over him. Dean was coming with him. He stepped out of the kitchen. He stopped outside the doorway and leaned against the wall.

Sam watched Cas disappear into the hall. He waited for a few seconds before he turned to Dean. "So you and Cas."

"...yeah." Dean's face went red. Oh god. Here it was. What was Sam going to say? Jesus christ, what was _everyone_ going to say when they found out?

Sam watched Dean's face go through a whirlwind of emotions. He expected annoyed and embarrassed and even mildly pissed off but he hadn't expected that fleeting look of sudden fear. Well, there went all the fun. He couldn't tease someone who looked like that, even if it was Dean. He leaned back on the counter. "You okay?"

"...ah...yeah...I...umm..." Dean found something very interesting to stare at on the floor. He waited for Sam to say something. And waited and waited and waited. Then took a quick glance up. Sam was just...leaning on the counter. Sam...wasn't saying anything...and...and he didn't look like he was going to. Oh.

Sam knew he could out stubborn Dean if he was quiet and didn't make any sudden movements. Dealing with Dean and his emotions was a lot like dealing with stray cats. Why was his brother always so weird? He still didn't get why Cas wanted to put up with that. Well at least they could be weird together instead of dragging two sane people down with them.

Dean took another sideways glance at Sam. Okay. Sam wasn't going to say anything. And...and really what _was_ there to say? _It was Cas_. Dean dropped his eyes down again and rubbed at his neck, "Thanks for....uh....not making a big deal out of this."

Sam fought the urge to roll his eyes. Did Dean think this was the first time anyone had figured out what was going on with him and Cas? Did he seriously think everyone in the bunker _hadn't_ seen him and Cas stare at each other before? Sam studied him for a moment. Yep. That was exactly what Dean thought. Sam wanted to say something supportive but he knew Dean. Unless things were about to blow up in his face he wasn't going to take a heart to heart moment seriously. "You're not going to help me with the dishes are you?"

Dean looked up and grinned, "Nope."

Sam shook his head, chuckling, as Dean made a quick get away before someone could talk about feelings. The laughter stopped when he realized not only would he have to do the dishes he'd probably have to clean the rest of the bunker too. Damn it. He should have blackmailed Dean when he had the chance. Why did he have to clean up _everything_ in the bunker?

Dean rounded the corner and slammed into Cas. Cas stared at him, searching for something in his eyes. Dean stared back. Cas leaned in close and pressed the most awkward open-eyed kiss against his lips. It was so Cas, his creepy stalker angel.

Cas leaned back. He watched Dean for a moment. "I _like_ you."

Dean shrugged confused. Well yeah, it was kind of obvious Cas liked him. Why else would someone be creeping around in the hallway eavesdropping wearing his robe after they'd been screwing all night? ...okay, he was gonna have another talk with Cas about social norms. Later. "Ah...yeah, Cas, I like you too."

"Good." Cas nodded his head pointedly. He'd take Charlie's advice and work Dean up to _'big L's'_ slowly. He spun around on his heel. He started for his room, only pausing for a moment before he heard Dean following him.

Cas opened the door to his room, crossing the floor in the dark to turn a bedside lamp on. He turned back to see Dean shifting on his feet in the doorway. It struck him as humorous that Dean was nervous to come into his room after they'd spent the night together. Cas waited for Dean to move but Dean stayed where he was. Maybe this was too sudden a transition for Dean? Dean often reacted negatively to change. Maybe Dean needed that strange human thing: _'space'_. Cas stepped closer to Dean, "You don't _have_ to sleep here today, Dean."

Dean jumped when Cas spoke up. He stared at Cas because really, holy crap, _there's_ **_Cas_**. Then thought over what Cas had said. His face scrunched up. What? That was ridiculous. He pushed pass Cas and into the room. "Where else am I going to sleep?"

Cas didn't mention the dozens of other bedrooms in the bunker. He slipped Dean's robe off and folded it up. He set it down on top of his dresser. When he turned around this time Dean was in _his_ bed adjusting the pillows. He waited for Dean to arrange things to his liking before turning off the lamp and getting into bed. Cas laid still. He took in a sharp breath when he felt Dean's fingers tentatively brush against his arm. Dean yanked his hand back at his sudden movement but a moment later it was back and pulling him to the centre of the bed.

Dean pulled Cas closer, curling around him. He buried his face in Cas's hair and breathed. His nose twitched. _That_ was the weird smell. He squirmed away, "Dude, you smell like my _brother_."

"What?" Cas had forgotten about that moment in the shower already– human memories were not as reliable it seemed. "Oh.... Yeah, I used his shampoo this morning."

"Roll over." Dean pushed gently at Cas's side. No way could he sleep with that ridiculous fruity smell in his nose.

"...okay?" Cas rolled over wondering what Dean– Oh. Dean wriggled closer to him until he was pressed up against his chest and his butt in his lap. Dean rocked his hips back once. Cas squinted at the back of Dean's head. Did Dean want sex? He slowly pressed his own hips forward. Dean chuckled but didn't move again. Cas wasn't sure what it meant but it apparently didn't mean sex. It was probably for the best. He didn't think his stomach would be capable of handling even _mild_ activity at the moment. He settled his hand on Dean's hip. Dean hissed.

"Dude. Not there." Dean nudged Cas's hand a little lower. "You left some wicked bruises behind."

Cas moved his hand down to Dean's leg. "You told me to grab harder."

"I was drunk. I also told you to always take your socks off first." Dean rubbed at his nose, that stupid fruity smell _lingered_. He mashed his face into the pillow and breathed deep a few times. Good. Now all he could smell was Cas.

Removing someone's socks first had actually seemed the most reasonable thing Dean had said for much of the night. Cas narrowed his eyes. If Dean had been lying about the socks..."Were you making up the baseball metaphors?"

"No. No, those are totally real." Dean laughed. Oh god, he wished he had a picture of the face Cas had made when he found out second base was from baseball.

Cas wasn't sure if he believed that. He'd ask Sam tomorrow. Cas shifted, moving the arm underneath himself up in order to rest his head on it and, better yet, to curl the rest of it around the top of Dean's head. He pressed his face to the back of Dean's neck.

There was a long sigh from both of them.

This was best freakin' way to sleep off a hangover ever. Dean closed his eyes enjoying how the little puffs of air against the back of his neck slowed and evened out. He could feel Cas's body relaxing into sleep. Dean reached down and pulled Cas's arm up from his leg and brought it around to tuck it in against his chest. He could say with 100% certainty that he hadn't _planned_ this but he wasn't dense. It had been a long time coming.

**Notes for the Chapter:**

> There's now a fore real Epilogue! But I'll leave this one here in case you don't want to read a longer discussion about STIs. So yeah, if STIs make you uncomfortable stop here. If not proceed!
> 
> Epilogue: Dean is nothing if not responsible. He has a huge awkward discussion with Cas about STIs and then goes to get tested because like he said, mostly sure isn't 100% sure. 
> 
> However I'm sure he probably also told Cas he was getting tested for something ridiculous as well, like Lollipop Disease. Oh the terrible double entendres.


	7. Epilogue: Two can play this game.

**Summary for the Chapter:**

> Dean thinks he's funny. Cas has his revenge. Also there's sex.

**Notes for the Chapter:**

> ****Warning for a discussion about sexually transmitted infections.****  
> It's nothing too graphic but I thought I'd warn people in advance.
> 
> Where can you find me? [Brains for baby jesus](http://brainsforbabyjesus.tumblr.com/). Won't you buy my brains?

Dean laid in bed- _Cas's bed_ \- and stared at Cas. How was he supposed to bring this up? It was one thing to say, hey, I'm gonna go get tested see you in a bit. _That_ he could say. That was easy. But how did he say, I'm gonna go get tested and you're coming with me? Well he could just _say_ that he guessed. It was just that....well....that sounded a lot like, hey I think you were lying about never having sex before.

He didn't _really_ think Cas was lying about last week being his first time but Jimmy Novak could have left behind a few surprises for Cas when he died and Cas went mortal. How much did Cas really know about Jimmy any way? Maybe Jimmy had secretly been a sex addict getting down and dirty with hookers in alleyways and truck stops. Dean chuckled to himself at the mental image. Jimmy Novak having nasty alleyway sex with hookers behind truck stops? Yeah right.

A slight shake of the bed woke Cas up. He stretched his legs out straight until his knees popped. That was a strange new thing his body had been doing lately. It felt good even if it sounded unsettling. He rolled onto his side, curling his hands up between himself and Dean. He breathed out a deep relaxed sigh. He still wasn't dreaming up this past week. He smiled, "Good morning Dean."

"Mornin' Cas." Dean's hand shot out involuntarily to brush the hair back on Cas's forehead. God damn that felt nice. Maybe he'd just do that some more... He ran his hand through Cas's hair a few more times, then along Cas's side, then back up his arm, and he had kind of developed an obsession about touching Cas in the morning.

Cas rolled around until he was facing away from Dean then squirmed in closer to him. Dean grabbed Cas around the middle and pulled him in tight against his chest. He was definitely more than happy to accommodate the new position. It gave him the perfect opportunity to take advantage of his morning wood and Cas's butt. He wriggled around a bit more until he had his dick pressed between Cas's butt cheeks. He gave a few friendly good morning thrusts. Cuz, you know that was how everyone said good morning, right? Well that was what he had been trying to convince Cas of all week. He didn't think Cas was _actually_ falling for it. It probably had more to do with how he was sliding his hand along Cas's chest and down his stomach until he conveniently found something to do with his hand. And okay, so maybe his touching Cas in the morning obsession was more a having morning sex with Cas obsession. Hey, it was still touching if he grabbed Cas's dick, right? Just a really sexy touch.

Cas let out a soft moan when Dean's hand wrapped around his penis. He wondered how many times they had to do this before it was considered a morning tradition. He set his hand down on Dean's wrist following along with the methodical strokes. His skin prickled as Dean breathed against the back of his neck. Yes, he wouldn't mind at all if they did this every morning indefinitely.

The little noises and twitches Cas made as he jerked him off made his dick stand up the rest of the way at a attention. Dean gasped when one of Cas's twitches was more of a jump. That jump had sent his dick sliding between Cas's thighs. Cas froze. Shit, had he rammed his dick into Cas's balls or something? Man, that would totally put a damper on the morning sexy times.

"You- ah- alright?" Dean asked trying to stay still because if Cas was alright he was definitely going to take advantage of the situation. Get himself some inter...crustat- cruxta- cunei- fuck it. Thigh sex. He was totally going to have hot morning thigh sex if Cas was up for it.

"Yes." Cas said while he experimentally squeezed his legs tighter together. He didn't want to hurt Dean with too much pressure. Dean didn't say anything or pull away as he pressed his legs together. He slowly moved his hips. Dean's penis slid along all that wonderfully soft sensitive skin behind his testicles– Dean had been adamant all week he call them balls but that was ridiculous. If anything they were more egg shaped. Maybe he should start calling them ovoids?

Cas lost tract of his inner debate over ovoids when Dean started moving his hand again. He breathed in sharply when Dean tightened his grip just a little more, "Yes, I'm alright. I'm..."

Dean chuckled as Cas forgot he was talking. He nibbled at the back of Cas's neck, still pumping his hand and thrusting between Cas's legs, "You're....?"

"Hmmm?" Cas asked, eyes closed and blissfully unaware of anything but Dean.

"You're alright and...?" Dean prompted again. Cas shivered as he licked up the back of Cas's neck.

"You're....enjoying yourself? Having a good time?" Dean offered. He flicked his tongue in behind Cas's ear. Cas let out a breathy whine. Dean craned his head up as far as he could to drag Cas's earlobe through his teeth.

" ** _Yes_**. Yes. I'm _enjoying_ that." Cas hissed out. Dean dropped his head back down and chuckled behind him. Puffs of air buffeted up against his neck making his hair stand on end with the pleasure of it all.

Dean grinned deviously, "You sure?"

"Yes." Cas's hips snapped up when Dean started sliding his thumb over the glands of his penis on every upstroke.

" _Really_ sure?" Dean asked as his thumb was coated in pre-come.

"Yes, Dean. I'm _really_ sure." Cas rolled his eyes despite how _very_ good it felt to have Dean touching him, "Please stop asking. I'll tell you if I'm not."

Dean chuckled to himself. He might not remember every little detail from _The_ Night but he did remember Cas getting all huffy about being asked too many questions when he just wanted to get laid.

Dean closed his eyes and listened to the noises Cas made. Lick the back of his neck? That was a whimper. Bite his shoulder? That got a whine. Pumping his dick just the right way? That was a gasp and sometimes his name. That always gave him a little thrill when Cas gasped out his name.

"Ah...Dean?"

Except for when Cas said it like that. Dean's eyes flicked open hearing the concern in Cas's voice.

"It's umm...starting to burn." Cas said relaxing his thighs. As nice as it had felt at first the friction of barely moistened skin dragging along against his own sensitive skin was fast becoming painful.

"Shit." Dean flopped onto his back to look over at the nightstand on his side. No lube. He lifted his head up. There it was. _All_ the way over _there_ on the night stand on Cas's side of the bed. He rolled over, straddling Cas, and reached for the lube. He felt one of Cas's hands delicately touch his side then lightly slide up and down. He smiled to himself. Cas was all business about touching his dick but he was still shy about touching him anywhere else. Guess he was still worried about those fading bruises on his hips.

Dean rolled off of him but didn't lay back down beside him. Except for a knee in his back Dean wasn't touching him at all. Cas craned his head around to see what Dean was doing. Dean licked his lips and smiled wide at him before running a hand slick with lube down his penis. Cas breathed in sharply. Of the very many possible things he had learned this past week that Dean could do watching Dean touch himself, without fail, had sent a thrill of excitement through him every time.

Dean flashed another grin at Cas before plunging a lubed up hand between Cas legs. He bit at his lip as Cas squirmed and gasped while he teased him. He _definitely_ liked knowing that he could make Cas, Scowly McGlaresALot, do that. He slid his hand up a little further and hesitated. He was right there...if he just...slid his hand up a little more.... He slowly brought his hand up until he had his fingers pressing over Cas's hole.

Cas shivered and stopped moving. Dean leaned over to see if it had been a good shiver or a bad shiver, "Can I....?"

"We don't have condoms in here."

Dean eyes went wide. Talk about getting straight to business, "Whoa, I didn't mean lets have a bunch of buttsex before breakfast....I just thought, you know, maybe we could try out a little bit-" He pressed his fingers against Cas, "-of that first and see if you like it. You know, build up to it."

"Oh." Cas pressed his hips back against Dean's hand. He wanted to try being the penetrated partner during sex but perhaps Dean was right. Maybe they _should_ build up to it. Their previous foray into intercourse was already confusing as it was. They had, as Dean put it, gone all the way but since then they had done nothing more than manual intercourse. He had gleaned enough from movies and books to know they had skipped some things when it came to developing a physical relationship. So yes, maybe Dean was right....but he still wanted to try it, "Alright."

Dean teased Cas for a few more moments, pressing over and sliding across his hole, until slipping a finger most of the way in. Cas let out a sound like all the air had gone out of him and thrashed his hips back pushing Dean's finger in the rest of the way. Dean grinned. That cleared up the question of whether Cas liked it or not.

Dean grinned as Cas made all sorts of quiet gasps. Yeah, Cas definitely liked that. Oh the things he was going to do to Cas now that he knew Cas liked it. Cas gave a soft moan. Dean licked his lips and tried to work in another finger. Cas's hips jerked backward. Yeah, there were terrible dirty things to be done. Awesome.

Dean worked his fingers in and out a few more times before deciding there was definitely a better way to do this. Cas let out a sad little whine when he took his finger out. He tugged at Cas, "Come on. Up."

Cas pushed himself up. He was about to ask why they needed to move, he was perfectly happy with the previous position, but then Dean pulled him closer until he was straddling Dean's lap. Cas wasn't sure what to do with his hands this way. He tried doing what Dean had done, putting them on Dean's neck, but that felt awkward. He let his hands fall to Dean's shoulders. That felt more natural. His entire body jolted when Dean wrapped a hand around his penis but not just because of Dean's _hand_. He looked down quickly. Dean had his hand around _both_ of them. He took in a sharp breath as he watched Dean pump his hand, pressing them together.

There wasn't much Dean could do to stop the shit-eating grin from dancing across his face. He had sort of suspected Cas had a thing for watching- as if years of staring hadn't tipped him off- but the way Cas had the laser eyes going on while he watched him stroke both their cocks in one hand was giving him ideas again. He shivered as the thought of tying Cas down and making him watch went through his head. Fuck. He really hoped Cas would go for something like that because now that it was in his head he wasn't going to stop thinking about it. Cas getting all hot and bothered watching him jerk off? Fuck. Yes please. He'd take two of those.

Dean leaned forward trying to get his free hand back to Cas's butt. Every time he got close Cas would fidget in his lap, "Don't move around so much."

"I'm not moving around."

"You are _so_ moving around."

"No, I'm not."

"Just sit still for a second."

"I am. _You're_ moving **me**."

Dean shook his head and rolled his eyes. He let go of their dicks for a second and held Cas still with one hand while he got his fingers back in Cas's butt, no thanks to Cas and his squirming around.

Cas took in a quick breath when Dean's fingers slid inside him. If being penetrated with fingers felt like this.....he shivered again. He hoped that they built up to intercourse again in the near future. His eyes flicked down again when Dean wrapped his hand around both of them once more. He groaned when Dean started pumping his hand and sliding his fingers in and out.

"Like that?" Dean asked watching Cas breath open mouthed and hard. Cas nodded his head but didn't take his eyes off their dicks, "Like watching?"

"Yes." Cas breathed out, "It's....very fascinating."

"Don't know if I'd use the word fascinating." Dean chuckled. He pumped his hand a little faster. He was starting to get good at figuring out when Cas was getting close, "Gonna have a climactic moment soon?"

Cas nodded. It was all he could do as Dean pressed his fingers further in. He watched the way his penis slid along side Dean's all in _Dean's hand_.

Dean stopped chuckling when his own breath started coming hard. A quick glance at Cas, and yup, Cas was running along that same edge with him. He stopped working his fingers, instead letting Cas rock back onto them, and squeezed their cocks a bit tighter. That deep groan Cas had started rumbling out of his throat. Fuck, that was hot. Cas groaned again. Holy fuck, yes! Just a little more of that!

Despite knowing that it was building up Cas was caught off guard by his orgasm every time with Dean. He knew it was building up. He knew he was so very close to climaxing but then suddenly he _was_ climaxing and that **_feeling_** just washed through him without warning. His eyes went wide when Dean pushed his fingers in a bit further and hit a particularly pleasurable spot. It felt like someone had run a match up his spine. He groaned as that feeling like a million little snaps of pleasure started all over again.

Dean figured he must have hit the sweet spot because suddenly Cas went from getting off is great to gasping for breath and twitching like a bug. He kept stroking Cas right along with his own cock until he was tumbling off that cliff right behind Cas. Twitching like a bug had its merits.

They sat still breathing hard letting the aftershocks of getting off pulse through them but Dean kept an eye on Cas. Dean had learned two days into this thing they had going on that Cas just didn't care how much of a mess they made. Dean on the other hand preferred to not be covered in jizz. When Cas looked like he was about to slump forward Dean pushed him gently back to the bed. He watched Cas flex his fingers and toes with that goofy blissed out smile on his face for a minute then reached over for the kleenex. He started wiping himself off.

Why did every time with Cas end up being such a mess? Sure they were both guys but it wasn't like there could be _that_ much jizz in either of them. Dean swore it multiplied afterwards when he wasn't looking. He scrubbed the kleenex across his stomach....and his chest and hand and....holy fuck one of them had gotten some distance because that was definitely come on the side of his neck....or maybe he had just scratched there with the gooey hand.

Okay. This was _exactly_ why he had to have that STI road trip discussion he kept putting off. They kept getting each other's spunk all over themselves. It was practically asking for it if one of them had something. Dean tossed the box of kleenex to Cas and decided that he had put off the Safe Sex and STI clinic road trip talk long enough.

"Hey Cas?"

"Yes?" Cas pulled a few tissues from the box and started patting his stomach down. He found it was better to pat down and try to scoop the cooling semen off rather then rub and spread it further. He felt he had learned quite a few practical experiences in the last week to compliment his theoretical knowledge.

"Remember how I said mostly sure wasn't one hundred percent sure?" Dean rubbed at his neck then stopped because there was still something crusty on his hand. Ugh. He stole a kleenex off Cas and rubbed at his neck and hand.

"Yes." Cas turned his head and narrowed his eyes at the garbage can. It was on the other side of the room. He was starting to see why so many humans kept it close to the bed.

"Right so, I was thinking....we should...." Dean hesitated because it _really_ did sound like he was saying he thought Cas was lying about sex and Cas said he trusted him so he should trust Cas right? Fuck. How the hell did he do this? He almost rubbed at his neck again but caught himself. He sighed, might as well start at the beginning, "Okay, you know about STIs right?"

"Sexually transmitted infections. Yes. I'm aware." Cas said getting up to throw the used tissues out, "I am– was an angel, Dean. I'm aware of the _vast_ variety of infections that humans are susceptible to."

Dean cocked an eyebrow at Cas's tone. So he wanted to play the I'm an angel and I know everything card? Dean grinned. He put on a serious face before Cas turned around, "So you know about Lollipop disease, right?"

"Lollipop disease?" Cas's head tilted to the side. What on earth was Lollipop disease? Perhaps it was a colloquialism?

"Yeah. It's pretty serious." Dean said trying to keep an equally serious expression on his face, "It causes umm....excessive hair growth and...ah..." He tried to figure out some words to describe stealing porn that Cas might believe, "And cravings for visual stimulation of a sexual nature."

Cas mouthed the symptoms to himself. None of that matched any infection he could think of, "Those are very unusual symptoms. Is it an emerging....." Cas stopped and studied Dean's impassive face. He narrowed his eyes, "You're making it up."

"No I'm not. It's a serious problem." Dean said trying to hold back the grin that was threatening to give him away, "The worst part is that it causes premature ejaculation, cuz' it only takes three licks to get to the- ah...gooey centre."

Cas rolled his eyes. Dean had tried to convince him of a myriad of strange things since becoming human. Each more ridiculous than the last, "Sexually transmitted infections can be very serious Dean."

"I know. I'm being very serious." Dean tried to do his best serious Cas impression, "I am very seriously concerned about Lollipop disease. Nobody wants a _real_ hairy banana."

Cas studied Dean for a moment. He knew that Dean was going to keep trying to convince him of this ridiculous made up disease as long as he maintained that Dean was making it up. Perhaps if he tried a different tactic; give Dean a taste of his own medicine so to speak, "Yes I suppose that _would_ be very serious."

Dean nodded, getting ready to have a laugh at Cas's expense for falling for his joke. Sam and Cas made the best faces when they were annoyed.

"I suppose it would be just as serious as some of the more common sexually transmitted infections." Cas said casually as he went to his dresser and started picking out clothes, "Are you aware of the symptoms and complications commonly associated with gonorrhea?"

Dean figured it would be kind of awkward having a talk about STIs with a guy who had watched the first creatures drag themselves out of the primordial ooze and looked like a guy in his late thirties. He was wrong. It wasn't awkward. It was _horrifying_. He was starting to regret trying to play his little joke on Cas. Okay that was a lie he _did_ regret it. He should have just said he wanted them both to get tested and left it at that. But no, he had to joke around and now he was getting an in-depth angelic lecture about....He shivered in disgust.

Dean figured that once Cas finished describing every god awful thing about gonorrhea he'd stop but no. No, Cas didn't stop. Cas looked at him and grinned that barely noticeable to others but hugely freakin' obvious to Dean devious grin and _kept going_. Cas knew exactly what he was doing. Ugh, fuck you Cas, fuck you so hard. Dean hunched his shoulders together in disgust while Cas described festering sores. What the hell had Cas _done_ while he was an angel? Go around the world and ask to look at people's diseased junk? And he just kept going _on_. It didn't _stop_. Oh god, did he just say aneurysms? How did you get _aneurysms_ from sex?

Dean's eyes went wide. Cas _had_ to be playing his own joke on him now. People didn't really get aneurysms from sex....right? Dean gulped, "Aneurysms?"

"Yes. It's a possible complication of tertiary syphilis." Cas said pulling his shirt on.

Holy fuck.

Actually, this just in, jesus fucking christ: **_Aneurysms!?_**

"At any rate, I'm sure Lollipop disease is far more dangerous." Cas said as he buckled his belt and headed for the door. He paused in the doorway. He looked Dean over. Perhaps now Dean would stop making things up. Dean sat speechless on the bed. Cas licked his lips. Yes, Dean looked like he would think twice about it, "Do you want to make breakfast together?"

Dean nodded quietly and stared as Cas freakin' _sauntered_ out of the room looking smug as hell closing the door behind him. Yeah, that asshole knew exactly what he was doing. And fuck, it had worked. No way was he joking about sex with Cas anymore when Cas could just bust out the encyclopedia of gross. And aneurysms, seriously, what the hell was up with that?  

Dean shifted uncomfortably. He looked down at his dick. He looked at the kleenexes on the bed. He looked at the door. Aneurysms. _Freakin' hell Cas._ **Aneurysms!**

Dean scrambled to get dressed. So what if it sounded like he didn't believe Cas when he said last week was the first time he had sex? They could be catching sexually transmitted aneurysms from each other. Jesus fucking christ! He yanked clothes on not caring if they were his or Cas's. He tore the door open and jogged down the hall after Cas, "Cas! Hey! So, I was thinking we should totally get tested for everything."

**Notes for the Chapter:**

> I like writing Cas innocently discovering little kinks he has. He likes watching Dean anyway but watching Dean do something sexy? I imagine he'd like that very much. 
> 
> Also I like writing Cas being a sneaky shit. He may not be very good at making something up but he would harness the power of truth to serve his own devices like the angel he was. Angels: masters at manipulation.
> 
> If there's popular demand I may add another couple of chapters to this. So....thoughts? 
> 
> (Requests as to the content of these hypothetical chapters would be a nice starting point for more chapters. *wink* *wink* *nudge* *nudge*).


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